ASYMMETRIC-SYNTHESIS AND HIGHLY DIASTEREOSELECTIVE ORTHO-LITHIATION OF FERROCENYL SULFOXIDES - APPLICATION TO THE SYNTHESIS OF FERROCENYL DERIVATIVES WITH PLANAR CHIRALITY

被引：207

作者：

REBIERE, F

RIANT, O

RICARD, L

KAGAN, HB

机构：

[1] UNIV PARIS 11,INST CHIM MOLEC ORSAY,SYNTH ASYMETR LAB,CNRS,URA 1497,F-91405 ORSAY,FRANCE

[2] ECOLE POLYTECH,DCPH,CHIM PHOSPHORE & ELEMENTS TRANSIT LAB,F-91128 PALAISEAU,FRANCE

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1993年 / 32卷 / 04期

关键词：

D O I：

10.1002/anie.199305681

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantiomerically pure sulfoxides with planar chirality (3, R = tBu, p‐Tol, X = H) can be prepared by the asymmetric synthesis of sulfoxides 1, and subsequent diastereoselective deprotonation to give 2, X = H. Double deprotonation of 1, R = tBu, provided 2, X = Li, which could be converted into diphosphane 3, X = E = PPh2. (Figure Presented.) Copyright © 1993 by VCH Verlagsgesellschaft mbH, Germany

引用

页码：568 / 570

页数：3

共 18 条

[1] ASYMMETRIC DEPROTONATION AND COMPLEXATION REACTIONS MEDIATED BY CHIRAL KETALS AS A ROUTE TO ORTHO-DISUBSTITUTED (ETA-6-ARENE)CR(CO)3 COMPLEXES
AUBE, J
HEPPERT, JA
MILLIGAN, ML
SMITH, MJ
ZENK, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) : 3563 - 3570
[2] AN EFFICIENT AND DIASTEREOSELECTIVE METHOD FOR THE SYNTHESIS OF (R)-1-FERROCENYLETHYLAMINES AND 1-FERROCENYLETHYL ACETATE
DAVID, DM
KANEMAGUIRE, LAP
PYNE, SG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (12) : 888 - 889
[3] DESHMUKH M, 1985, TETRAHEDRON LETT, V26, P402
[4] A CONVENIENT FAMILY OF CHIRAL SHIFT-REAGENTS FOR MEASUREMENT OF ENANTIOMERIC EXCESSES OF SULFOXIDES
DESHMUKH, M
DUNACH, E
JUGE, S
KAGAN, HB
[J]. TETRAHEDRON LETTERS, 1984, 25 (32) : 3467 - 3470
[5] MIXED COUPLING BETWEEN VINYLIC SULFONES AND GRIGNARD-REAGENTS IN THE PRESENCE OF SALTS OF TRANSITION-METALS - STEREOSELECTIVE SYNTHESIS OF TRISUBSTITUTED OLEFINS
FABRE, JL
JULIA, M
VERPEAUX, JN
[J]. TETRAHEDRON LETTERS, 1982, 23 (24) : 2469 - 2472
[6] REACTIONS OF PYRIDYL AND QUINOLYL SULFOXIDES WITH GRIGNARD-REAGENT - A CONVENIENT PREPARATION OF PYRIDYL AND QUINOLYL GRIGNARD-REAGENTS
FURUKAWA, N
SHIBUTANI, T
MATSUMURA, K
FUJIHARA, H
OAE, S
[J]. TETRAHEDRON LETTERS, 1986, 27 (33) : 3899 - 3902
[7] ASYMMETRIC-SYNTHESIS CATALYZED BY TRANSITION-METAL COMPLEXES WITH FUNCTIONALIZED CHIRAL FERROCENYLPHOSPHINE LIGANDS
HAYASHI, T
KUMADA, M
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (12) : 395 - 401
[8] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-TRANSITION METAL-COMPLEXES .1. PREPARATION OF CHIRAL FERROCENYLPHOSPHINES
HAYASHI, T
MISE, T
FUKUSHIMA, M
KAGOTANI, M
NAGASHIMA, N
HAMADA, Y
MATSUMOTO, A
KAWAKAMI, S
KONISHI, M
YAMAMOTO, K
KUMADA, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (04) : 1138 - 1151
[9] HUDLICKY M, 1984, REDUCTIONS ORGANIC C, P88
[10] NUCLEOPHILIC DISPLACEMENT ON SULFUR . INVERSION OF SULFOXIDE CONFIGURATIONS
JOHNSON, CR
MCCANTS, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (23) : 5404 - &

← 1 2 →