Stereochemistry of enantioselective deprotonation of 4-substituted cyclohexanones by chiral bidentate lithium amides

被引：25

作者：

Toriyama, M

Sugasawa, K

Shindo, M

Tokutake, N

Koga, K

机构：

[1] NIHON UNIV,COLL PHARM,FUNABASHI,CHIBA 274,JAPAN

[2] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 04期

关键词：

D O I：

10.1016/S0040-4039(96)02373-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective deprotonation of 4-substituted cyclohexanones (1) in the presence of excess trimethylsilyl chloride was examined using chiral bidentate lithium amides ((R)-3 similar to(R)-7) in THF. The solution structures of (A)-3a in THF in the presence and in the absence of lithium chloride were studied by NMR. It is concluded that the eight-membered cyclic transition state (10) offers reasonable explanation of the stereochemical course of the present reaction using (R)-3a. (C) 1997, Elsevier Science Ltd. All rights reserved.

引用

页码：567 / 570

页数：4

共 21 条

[1]

[Anonymous], MODERN SYNTHETIC MET

[2]

[Anonymous], 1984, ASYMMETRIC SYNTHESIS

[3] ENANTIOSELECTIVE DEPROTONATION OF 4-SUBSTITUTED CYCLOHEXANONES BY CHIRAL CHELATED LITHIUM AMIDES HAVING A FLUORINE-CONTAINING ALKYL GROUP ON AMIDE NITROGEN [J].