STEREOCONTROL IN THE INTRAMOLECULAR NITRONE CYCLOADDITION TO VINYL SULFUR DERIVATIVES

被引：7

作者：

ANNUNZIATA, R ^{[1
]}

CINQUINI, M ^{[1
]}

COZZI, F ^{[1
]}

GIARONI, P ^{[1
]}

RAIMONDI, L ^{[1
]}

机构：

[1] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1990年 / 1卷 / 04期

关键词：

D O I：

10.1016/S0957-4166(00)86330-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The intramolecular cycloaddition to vinyl sulphur derivatives of a series of nitrones featuring an alkyl or alkoxy substituted α-stereocenter on the tether connecting dipole and dipolarophile occurs in a completely stereoselective fashion to give 3′,3-anti configurated products. The synthetic potentialities of this reaction is illustrated by the synthesis of a precursor of (d)-biotin. © 1990.

引用

页码：251 / 264

页数：14

共 20 条

[1] ANNUNZIATA R, 1989, GAZZ CHIM ITAL, V119, P253
[2] ANNUNZIATA R, 1988, TETRAHEDRON LETT, P2881
[3] SYNTHESIS OF D-BIOTIN FROM L-CYSTINE VIA INTRAMOLECULAR [3+2] CYCLOADDITION
BAGGIOLINI, EG
LEE, HL
PIZZOLATO, G
USKOKOVIC, MR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (23) : 6460 - 6462
[4] RECENT SYNTHETIC APPLICATIONS OF NITRONES - A REVIEW
BALASUBRAMANIAN, N
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1985, 17 (01) : 23 - 47
[5] TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING
CARON, M
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) : 1557 - 1560
[6] Confalone P. N., 1988, ORG REACTIONS, V36, P1
[7] A SIMPLE AND ENANTIOSELECTIVE SYNTHESIS OF (+)-BIOTIN
COREY, EJ
MEHROTRA, MM
[J]. TETRAHEDRON LETTERS, 1988, 29 (01) : 57 - 60
[8] ENANTIOSELECTIVE SYNTHESIS OF THE KEY INTERMEDIATE OF A 1-BETA-METHYLCARBAPENEM ANTIBIOTIC BY WAY OF NITRONE 1,3-DIPOLAR CYCLOADDITION
IHARA, M
TAKAHASHI, M
FUKUMOTO, K
KAMETANI, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (12): : 2215 - 2221
[9] NOVEL E-Z EQUILIBRIUM OF "N-ALKYL-ALPHA-ALKOXYCARBONYLNITRONE IN SOLUTION
INOUYE, Y
HARA, J
KAKISAWA, H
[J]. CHEMISTRY LETTERS, 1980, (11) : 1407 - 1410
[10] KNUNYANTS IL, 1964, IAN SSSR KH, P644

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