STEREOCONTROLLED SYNTHESIS VIA CHIRAL AZIRIDINES

被引：81

作者：

TANNER, D

机构：

[1] Dept. of Organic Chemistry, University of Uppsala, S-751 21, Uppsala

来源：

PURE AND APPLIED CHEMISTRY | 1993年 / 65卷 / 06期

关键词：

D O I：

10.1351/pac199365061319

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The use of chiral, non-racemic, aziridines for stereochemical control in diastereo- and enantioselective synthesis is described. Such aziridines are readily available in quantity from the corresponding chiral epoxides, and can be utilised: (i) as chiral substrates, e.g. for the enantioselective synthesis of carbapenem antibiotics and non-proteinogenic amino acids; (ii) as efficient chiral auxiliaries for diastereoselective enolate alkylation and aldol reactions; (iii) as chiral ligands, e.g. for enantioselective OsO4-mediated 1,2-dihydroxylation of olefins.

引用

页码：1319 / 1328

页数：10

共 50 条

[41] The synthesis of chiral β-ketosulfoxides by enantioselective oxidation and their stereocontrolled reduction to β-hydroxysulfoxides
Cardellicchio, C
Hassan Omar, O
Naso, F
Capozzi, MAM
Capitelli, F
Bertolasi, V
TETRAHEDRON-ASYMMETRY, 2006, 17 (02) : 223 - 229
[42] STEREOCONTROLLED SYNTHESIS OF (+/-)-RECIFEIOLIDE VIA ORGANOPALLADIUM CHEMISTRY
TROST, BM
VERHOEVEN, TR
TETRAHEDRON LETTERS, 1978, (26) : 2275 - 2278
[43] STEREOCONTROLLED SYNTHESIS OF (+/-)-MODHEPHENE VIA THE WEISS REACTION
WROBEL, J
TAKAHASHI, K
LANNOY, G
COOK, JM
BERTZ, SH
HONKAN, V
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (01): : 139 - 141
[44] STEREOCONTROLLED SYNTHESIS OF (+)-SARRACENIN VIA PHOTOCHEMICAL CYCLOADDITION
TIETZE, LF
GLUSENKAMP, KH
NAKANE, M
HUTCHINSON, CR
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (01): : 70 - 71
[45] ASYMMETRIC-SYNTHESIS .13. THE STEREOCONTROLLED SYNTHESIS OF (R)-ALPHA-AMINO ACIDS VIA A DOUBLE CHIRAL INDUCTION
JIANG, YZ
LIU, G
ZHOU, CY
PIAO, HR
WU, LJ
MI, AQ
SYNTHETIC COMMUNICATIONS, 1991, 21 (8-9) : 1087 - 1090
[46] Highly Stereocontrolled Formal Synthesis of Brassinolide via Chiral Sulfoxide-Directed SN2' Reactions
Marino, J. P.
De Dios, A.
Anna, L. J.
Fernandez De la Pradilla, R.
Journal of Organic Chemistry,
[47] Stereocontrolled synthesis of chiral oxa- and azacycles via asymmetric horner-wadsworth-emmons reactions.
Rein, T
Vares, L
Kawasaki, I
Lühdorf, A
Nielsen, K
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U95 - U96
[48] Highly stereocontrolled formal synthesis of brassinolide via chiral sulfoxide-directed S(N)2' reactions
Marino, JP
deDios, A
Anna, LJ
delaPradilla, RF
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01): : 109 - 117
[49] Synthesis of Chiral Aziridines Through Decarboxylative Generation of Sulfur Ylides and Their Reaction with Chiral Sulfinyl Imines
Forbes, David C.
Bettigeri, Sampada V.
Amin, Sejal R.
Bean, Christie J.
Law, Amanda M.
Stockman, Robert A.
SYNTHETIC COMMUNICATIONS, 2009, 39 (13) : 2405 - 2422
[50] On the utility of S-mesitylsulfinimines for the stereoselective synthesis of chiral amines and aziridines
Roe, Caroline
Sola, Toni Moragas
Sasraku-Neequaye, Leonid
Hobbs, Heather
Churcher, Ian
MacPherson, David
Stockman, Robert A.
CHEMICAL COMMUNICATIONS, 2011, 47 (26) : 7491 - 7493

← 1 2 3 4 5 →