2ND-GENERATION AUXILIARY FOR THE ASYMMETRIC ADDITION OF METALATED TETRAHYDROISOQUINOLINES TO ALDEHYDES

被引:19
作者
ZHANG, PS [1 ]
GAWLEY, RE [1 ]
机构
[1] UNIV MIAMI,DEPT CHEM,CORAL GABLES,FL 33124
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(00)79567-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The selectivity of asymmetric addition of tetrahydroisoquinolyloxazoline Grignard reagents to aldehydes has now been improved to 78-82% ds through the use of a camphor-derived auxiliary. The new auxiliary has broad applicability, with overall yields of chemically and diastereomerically pure addition products now in the 50-58% range.
引用
收藏
页码:2945 / 2948
页数:4
相关论文
共 20 条
[1]   CONCERNING PURITY OF MAGNESIUM AND BERYLLIUM ALKYLS AND HALIDES PREPARED BY DIFFERENT METHODS [J].
ASHBY, EC ;
ARNOTT, RC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1968, 14 (01) :1-&
[2]   DIPOLE-STABILIZED CARBANIONS - NOVEL AND USEFUL INTERMEDIATES [J].
BEAK, P ;
REITZ, DB .
CHEMICAL REVIEWS, 1978, 78 (03) :275-316
[3]   METALATION AND ELECTROPHILIC SUBSTITUTION OF AMINE DERIVATIVES ADJACENT TO NITROGEN - ALPHA-METALLO AMINE SYNTHETIC EQUIVALENTS [J].
BEAK, P ;
ZAJDEL, WJ ;
REITZ, DB .
CHEMICAL REVIEWS, 1984, 84 (05) :471-523
[4]   ASYMMETRIC ALDOL REACTIONS - A NEW CAMPHOR-DERIVED CHIRAL AUXILIARY GIVING HIGHLY STEREOSELECTIVE ALDOL REACTIONS OF BOTH LITHIUM AND TITANIUM(IV) ENOLATES [J].
BONNER, MP ;
THORNTON, ER .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) :1299-1308
[5]   SYNTHESIS OF R-LAUDANOSINE AND 9-R-O-METHYLFLAVINANTINE BY ASYMMETRIC ALKYLATION [J].
GAWLEY, RE ;
SMITH, GA .
TETRAHEDRON LETTERS, 1988, 29 (03) :301-302
[6]  
GAWLEY RE, 1991, COMPREHENSIVE ORGANI, V1, P459
[7]  
GAWLEY RE, 1991, COMPREHENSIVE ORGANI, V3, P65
[8]  
HIGHSMITH TK, 1991, ADV HETEROCYCL NAT P
[9]   CHEMISTRY OF CARBANIONS .2. REACTION OF ORGANOMAGNESIUM COMPOUNDS WITH ALPHA,BETA-UNSATUR1TED KETONES [J].
HOUSE, HO ;
EVANS, RA ;
TRAFICAN.DD .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (02) :348-&
[10]   INVESTIGATION ON DIASTEREOSELECTIVE C,C-BOND FORMATION IN THE 1-POSITION OF 1,2,3,4-TETRAHYDROISOQUINOLINES .2. EPC-SYNTHESIS OF TETRAHYDROISOQUINOLINES BY DIASTEREOSELECTIVE ALKYLATION AT THE 1-POSITION OF PHENYLALANINE-DERIVED PRECURSORS - SYNTHESIS OF THE ALKALOID (+)-CORLUMINE [J].
HUBER, IMP ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1987, 70 (07) :1944-1954