Enantioselective synthesis of optically active homoallylamines by nucleophilic addition of chirally modified allylboranes to N-silylimines

被引：37

作者：

Itsuno, S ^{[1
]}

Watanabe, K ^{[1
]}

Matsumoto, T ^{[1
]}

Kuroda, S ^{[1
]}

Yokoi, A ^{[1
]}

El-Shehawy, A ^{[1
]}

机构：

[1] Toyohashi Univ Technol, Dept Mat Sci, Toyohashi, Aichi 4418580, Japan

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 14期

关键词：

D O I：

10.1039/a902635e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselectivity in the allylboration of N-silylimines with a variety of chirally modified allylboron reagents has been examined. Optically active N-sulfonylamino alcohols (16, 17 and 19) derived-from D-camphor and norephedrine were found to be efficient chiral ligands for the allylboration reagent. These reagents:smoothly reacted with N-silylimines to give the corresponding homoallylic amines in a high level of enantioselectivity up to 96%ee.

引用

页码：2011 / 2016

页数：6

共 35 条

[1] Preparation and use of aziridino alcohols as promoters for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines
Andersson, PG
Guijarro, D
Tanner, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) : 7364 - 7375
[2] ENANTIOSELECTIVE SYNTHESIS OF HOMOALLYLIC AMINES BY ADDITION OF ALLYLMETAL REAGENTS TO IMINES DERIVED FROM (S)-VALINE ESTERS
BASILE, T
BOCOUM, A
SAVOIA, D
UMANIRONCHI, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) : 7766 - 7773
[3] THE BORON APPROACH TO ASYMMETRIC-SYNTHESIS
BROWN, HC
RAMACHANDRAN, PV
[J]. PURE AND APPLIED CHEMISTRY, 1991, 63 (03) : 307 - 316
[4] ASYMMETRIC CARBON CARBON BOND FORMATION VIA BETA-ALLYLDIISOPINOCAMPHEYLBORANE - SIMPLE SYNTHESIS OF SECONDARY HOMOALLYLIC ALCOHOLS WITH EXCELLENT ENANTIOMERIC PURITIES
BROWN, HC
JADHAV, PK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) : 2092 - 2093
[5] B-ALLYLDIISOCARANYLBORANE - A NEW, REMARKABLE ENANTIOSELECTIVE ALLYLBORATING AGENT FOR PROCHIRAL ALDEHYDES - SYNTHESIS OF HOMOALLYLIC ALCOHOLS APPROACHING 100-PERCENT ENANTIOMERIC PURITIES
BROWN, HC
JADHAV, PK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) : 4089 - 4091
[6] Cainelli G, 1996, SYNLETT, P657
[7] Chataigner I, 1998, SYNLETT, P275
[8] Chen GM, 1999, ANGEW CHEM INT EDIT, V38, P825, DOI 10.1002/(SICI)1521-3773(19990315)38:6<825::AID-ANIE825>3.0.CO
[9] 2-V
[10] A PRACTICAL AND EFFICIENT METHOD FOR ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES
COREY, EJ
YU, CM
KIM, SS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) : 5495 - 5496

← 1 2 3 4 →