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Accounts and 2000
Rapid Communications in No. 12
Synthetic Organic Chemistry December
1699
The Paternò-Büchi Reaction of N-Acyl Enamines
Accounts
O O H O
and Aldehydes - The Development of a New Syn- 3
Ph H
thetic Method and its Application to Total Synthesis HOOC NH2 2 N
N O
and Molecular Recognition Studies O H H
T. Bach HO N O
O O
N
Me
1708
Acyl Phosphate Esters: Charge-Directed Acylation O O
and Artificial Blood O O
P C
N
H3CO OH H
R. Kluger P C
O H 3C
H3CO O H2N
O H CH3 H
N
H
H N
H
H
1721
Highly Stereoselective Conjugate Additions of
Letters
O O R2 O
Heteroaryl Alkyl Sulfoxides S
1. LHMDS, THF, -78 °C
S
Het 2. R2CH=CHCOR3 Het R3
M. Casey, R. S. Gairns, G. M. Geraghty, C. J. Kelly, P. J. Murphy,
A. J. Walker R1 R1
Het = 1-Methyl-2-imidazolyl or 2-pyridyl
1725
Synthetically Useful Desulfurisation Reactions of O R1 R1 R1
Heteroaryl Sulfoxide Conjugate Adducts S COR2 Heat or COR2 COR2
Het or
M. Casey, R. S. Gairns, A. J. Walker Nickel
Ph boride Ph Ph
Het = 1-methyl-2-imidazolyl or 2-pyridyl
1729
Titanium-Mediated Diastereoselective Formation of i-PrO
HO
O Ti Oi-Pr OH
(Z)- 1-(1-Alkenyl)-2-substituted-cyclopropyl Esters
Efficient Precursors of (Z)- 2,3-Methanoamino Acids O
( de: 100%)
S. Racouchot, J. Ollivier, J. Salaün HO NH2
COOH
(Z)-2,3-Methanobishomoserine (de: 100%)
IV Table of Contents
1733
Synthetic Studies on Pectenotoxins: Synthesis of the
Letters
8
OTBS
Common C8-C18 THF Fragment TBDPSO
H
D. Awakura, K. Fujiwara, A. Murai pectenotoxins
TBSO 11 O 14 18
BnO OH OMPM
C8-C18 THF fragment 1
1737
Highly Functionalised Difluorinated Cyclohexenols OH
O
OH 6 steps F
P. J. Crowley, A. C. Moralee, J. M. Percy, N. S. Spencer F
F
F3C O O
F
O O
1741
Synthesis of trans-(2-Aminocyclopropyl)alanine -
A Key Constituent of the Novel Antitumor Antibio-
tic Belactosin A
M. Brandl, S. I. Kozhushkov, K. Loscha, O. V. Kokoreva, D. S.
Yufit, J. A. K. Howard, A. de Meijere
1745
First Enantioselective Synthesis of Dendrobatid
CH3 nucleophilic CH3
Alkaloids Indolizidine (–)-209I and (–)-223J 1745 1,2-addition H
D. Enders, C. Thiebes α-alkylation
N N
N
R 209I: R = n-Pr
H3CO
223J: R = n-Bu
de = 96 − > 99%, ee > 99%
1749
Selective Synthesis of Unsymmetrical 3,4-Disub- R
stituted and 4-Substituted 2(5H)-Furanones Ar
O
R. Rossi, F. Bellina, E. Raugei Br Br O
Br Ar (R = Me, aryl)
O O
O O Ar
O
O
1753
The (2-Phenyl-2-trimethylsilyl)ethoxycarbonyl O .
TBAF 3H2O
(Psoc) Group - A Novel Amino Protecting Group R NH
CH2Cl2
O R NH2
M. Wagner, S. Heiner, H. Kunz SiMe3 r.t.
10-15 min
Table of Contents V
1757
A New and Effective Method to Carbazoquinocin C
Letters
and Related Carbazole-3,4-quinones as Biological
Antioxidants: Key Reactions of 2-Vinylindoles with
Oxalyl Chloride
A. Aygün, U. Pindur
1761
Synthesis and Spectroscopic Characterization of the
Second Isomer of (C69N)2 (II) Heterofullerene
N. Tagmatarchis, K. Okada, T. Tomiyama, H. Shinohara
1765
cis-Mo(CO)4(Py)2: A Superior Reagent for the R3
R3
Preparation of h3-Allyl Molybdenum Complexes (a) Mo(CO)4(Py)2, THF, ∆ R 1 Me
R1 Me
A. Kuhl, J. A. Christopher, L. J. Farrugia, P. J. Kocienski (b) LiCp, rt R2 Mo(CO)2Cp
R2 OCOR
60-94%
1769
Asymmetric Nucleophilic Addition to Vinylphos- O O R
phonates (Part I) P P
O O
K. Afarinkia, H. M. Binch, E. De Pascale N CHPh2 N CHPh2
d.e. upto 78%
1771
Asymmetric Nucleophilic Addition to Vinylphos- Ph O Ph O R
phonates (Part II) Me Me
P P
O O
K. Afarinkia, H. M. Binch, I. Forristal N N
CPh3 CPh3
d.e. upto 78%
1773
Simple Synthesis of 2-Substituted Tetrahydrofuran-
3-carbonitriles
M. Mπkosza, J. Przyborowski, R. Klajn, A. Kwast
VI Table of Contents
1775
CAL-B Catalyzed Enantioselective Synthesis of
Letters
Cyanohydrins - A Facile Route to Versatile Building
Blocks
U. Hanefeld, Y. Li, R. A. Sheldon, T. Maschmeyer
1777
Brønsted Acid-Catalyzed Hydration of Alkynes: cat. TfOH or Tf2NH O
A Convenient Route to Diverse Carbonyl R1 R2 + H2O R2
R1
Compounds 1,4-dioxane, 100 °C
T. Tsuchimoto, T. Joya, E. Shirakawa, Y. Kawakami R1, R2 = aryl, alkyl, acyl, alkenyl, H
1779
Reaction of 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes R1
with Aryl Isocyanates and Aryl Isothiocyanates R2
R1
A. P. Molchanov, D. I. Sipkin, Y. B. Koptelov, R. R. Kostikov N X
∆
+ R2 N C X N N
p-xylene
N N
R1 = MeO, Me, H, Cl; R2 = Ph, 4-ClC6H4, 1-Naphthyl; X = O, S
1781
A Novel Approach to Highly Substituted Enynes
Based on Thiophosphates
I. Maciπgiewicz, A. SkowroÒska
1783
Concise and Effective Synthesis of a(1Æ2)-Linked
Manno- and Rhamnopyranosyl Oligosaccharides
and Related Antigenic Factor 4 and Dominant of
Antigenic Factor 6
Y. Zhu, F. Kong
1788
Directed Metallation Studies on Heteroaromatic
Systems. Synthesis of 2,3-Disubstituted Furan,
Thiophene, N-Methylpyrrole and N-Methylindole
T. Grimaldi, M. Romero, M. D. Pujol
Table of Contents VII
1793
Intermolecular Pauson-Khand Reactions with
Letters
O OH
N-Alkynylamides – Electronically Tuned Variants Bn Ts
N
Bn
of Ynamines N
O Ts O
B. Witulski, M. Gößmann H
Bn Bn
N N H
Ts Ts H
1798
N-Bromosuccinimide (NBS), an Efficient Reagent
for the Conversion of 1,3-Oxathiolanes to Carbonyl
Compounds
B. Karimi, H. Seradj, M. H. Tabaei
1801
A Mild and Efficient Protocol for the Catalytic
Silylation of Aryl Bromides
L. J. Gooßen, A.-R. S. Ferwanah
1804
Dimsyl Anion Mediated Tandem Fragmentation
Cyclization Reactions of Alkenoyl Ketenedithioace-
tals: A Facile Synthesis of Substituted 2,3-Dihydro-
4H-thiopyran-4-ones
R. Samuel, S. K. Nair, C. V. Asokan
1807
Synthesis and Absolute Configuration of
(-)-Hyrtiosal
P. Basabe, A. Diego, D. Díez, I. S. Marcos, J. G. Urones
1810
Epoxidation of Olefins Mediated by Aliphatic
Ketiminium Salts +
N
BF4
S. Minakata, A. Takemiya, K. Nakamura, I. Ryu, M. Komatsu Oxone , NaHCO3
R2 (0.1 equiv) O
R1 R2
(1 equiv) H2O / MeCN, 25 °C R1
VIII Table of Contents
1813
The Reaction of Phenylselenenyl Triflate with Diazo
Letters
Compounds
M. Curini, F. Epifano, M. C. Marcotullio, O. Rosati
1816
Synthesis of Methano[60]fullerenephosphonic- PO3H2 PO3H2
and Methano[60]fullerene-diphosphonic Acids
H PO3H2
R. Pellicciari, B. Natalini, L. Amori, M. Marinozzi, R. Seraglia
5 8
1819
A New Allylidene Phosphorane Reagent for O EtO O O O
the Efficient Conversion of Aldehydes to R H
+ Ph3P
O R O
g,d-Unsaturated Allyl b-Ketoesters
D. Chapdelaine, P. Dubé, P. Deslongchamps
1822
Synthesis of Constitutionally Unsymmetric 7-Mem-
bered Biaryl Lactones by Ni-Mediated Intramolecu- O
lar Coupling O Ni(0)
O
G. Bringmann, J. Hinrichs, P. Henschel, K. Peters, E.-M. Peters Br O intramolecular
*
biaryl coupling
I
1825
A Highly Convenient New Methodology for the
Synthesis of N-Nitrosamines from Lithium Amides
N. S. Nudelman, A. E. Bonatti
1828
Chemoselective Imino Aldol Reaction Promoted R5 R5
by a Cation-Exchange Resin R1 OTMS N Cation-exchange NH O
+ resin
M. Shimizu, S. Itohara R2 R3 R4 H R4 R3
R1 2
R
Table of Contents IX
1831
Convenient Synthesis of (±)2-Thiazolidine Acetic
Letters
Acid Derivatives by Ring Contraction of 1,4-Thia-
zepine Derivatives
B. Zaleska,* D. Cieø
1834
Synthesis of meso Ferrocenyl Porphyrins Fc
S. J. Narayanan, S. Venkatraman, S. R. Dey, B. Sridevi, NH
H+ NH N
V. R. G. Anand, T. K. Chandrashekar Fc Fc
NH N HN
Fe
Fc
Fc = Ferrocenyl
1837
Synthesis of a Polyhydroxylated Tetrahydro-4H-
1,2,3-triazolo[1,5-a]azepin, a Higher Homolog of
“Nojiritriazole”, and of a Related C-Disaccharide
K. Tezuka, P. Compain, O. R. Martin
1840
Quaternary Ammonium Salt Catalyzed Azidolysis of 1. 10 mol% n-Bu4NCl
OH
Epoxides with Trimethylsilyl Azide O + Me3SiN3
2. p-TsOH, MeOH
C. Schneider 89% N3
1843
Addition of Pyrimidine and Purine Bases to Benzyl O O
2H-Azirine-3-carboxylate Me CO2Bn Me
NH K2CO3 NH
+ N
T. L. Gilchrist, R. Mendonça
N O N O
H
HN CO2Bn
1846
Supported Reagents: Opportunities and Limitations
in Synthesis
New Tools
G. Bhalay, A. Dunstan, A. Glen X
solid support reagent
X Table of Contents
1860
Triphosgene
Spotlight
Synlett
Compiled by D. Krishnaswamy
Indexes 2000 1861
Table of Contents XI
Author Index
Afarinkia, K. 1769, 1771 Forristal, I. 1771 Mπkosza, M. 1773 Salaün, J. 1729
Amori, L. 1816 Fujiwara, K. 1733 Maciπgiewicz, I. 1781 Samuel, R. 1804
Anand, V. R. G. 1834 Marcos, I. S. 1807 Schneider, C. 1840
Asokan, C. V. 1804 Gairns, R. S. 1721, 1725 Marcotullio, M. C. 1813 Seradj, H. 1798
Awakura, D. 1733 Geraghty, G. M. 1721 Marinozzi, M. 1816 Seraglia, R. 1816
Aygün, A. 1757 Gilchrist, T. L. 1843 Martin, O. R. 1837 Sheldon, R. A. 1775
Glen, A. 1846 Maschmeyer, T. 1775 Shimizu, M. 1828
Bach, T. 1699 Gooßen, L. J. 1801 Mendonça, R. 1843 Shinohara, H. 1761
Basabe, P. 1807 Gößmann, M. 1793 Minakata, S. 1810 Shirakawa, E. 1777
Bellina, F. 1749 Grimaldi, T. 1788 Molchanov, A. P. 1779 Sipkin, D. I. 1779
Bhalay, G. 1846 Moralee, A. C. 1737 SkowroÒska, A. 1781
Binch, H. M. 1769, 1771 Hanefeld, U. 1775 Murai, A. 1733 Spencer, N. S. 1737
Bonatti, A. E. 1825 Heiner, S. 1753 Murphy, P. J. 1721 Sridevi, B. 1834
Brandl, M. 1741 Henschel, P. 1822
Bringmann, G. 1822 Hinrichs, J. 1822 Nair, S. K. 1804 Tabaei, M. H. 1798
Howard, J. A. K. 1741 Nakamura, K. 1810 Tagmatarchis, N. 1761
Casey, M. 1721, 1725 Narayanan, S. J. 1834 Takemiya, A. 1810
Chandrashekar, T. K. 1834 Itohara, S. 1828 Natalini, B. 1816 Tezuka, K. 1837
Chapdelaine, D. 1819 Nudelman, N. S. 1825 Thiebes, C. 1745
Christopher, J. A. 1765 Joya, T. 1777 Tomiyama, T. 1761
Cieø, D. 1831 Okada, K. 1761 Tsuchimoto, T. 1777
Compain, P. 1837 Karimi, B. 1798 Ollivier, J. 1729
Crowley, P. J. 1737 Kawakami, Y. 1777 Urones, J. G. 1807
Curini, M. 1813 Kelly, C. J. 1721 Pellicciari, R. 1816
Klajn, R. 1773 Percy, J. M. 1737 Venkatraman, S. 1834
de Meijere, A. 1741 Kluger, R. 1708 Peters, E.-M. 1822
De Pascale, E. 1769 Kocienski, P. J. 1765 Peters, K. 1822 Wagner, M. 1753
Deslongchamps, P. 1819 Kokoreva, O. V. 1741 Pindur, U. 1757 Walker, A. J. 1721, 1725
Dey, S. R. 1834 Komatsu, M. 1810 Przyborowski, J. 1773 Witulski, B. 1793
Diego, A. 1807 Kong, F. 1783 Pujol, M. D. 1788
Díez, D. 1807 Koptelov, Y. B. 1779 Yufit, D. S. 1741
Dubé, P. 1819 Kostikov, R. R. 1779 Racouchot, S. 1729
Dunstan, A. 1846 Kozhushkov, S. I. 1741 Raugei, E. 1749 Zaleska, B. 1831
Krishnaswamy D. 1860 Romero, M. 1788 Zhu, Y. 1783
Enders, D. 1745 Kuhl, A. 1765 Rosati, O. 1813
Epifano, F. 1813 Kunz, H. 1753
Kwast, A. 1773 Rossi, R. 1749
Farrugia, L. J. 1765 Li, Y. 1775 Ryu, I. 1810
Ferwanah, A.-R. S. 1801 Loscha, K. 1741
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