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

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 21期

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

页码：2945 / 2948

页数：4

共 20 条

[1] CONCERNING PURITY OF MAGNESIUM AND BERYLLIUM ALKYLS AND HALIDES PREPARED BY DIFFERENT METHODS
ASHBY, EC
ARNOTT, RC
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1968, 14 (01) : 1 - &
[2] DIPOLE-STABILIZED CARBANIONS - NOVEL AND USEFUL INTERMEDIATES
BEAK, P
REITZ, DB
[J]. CHEMICAL REVIEWS, 1978, 78 (03) : 275 - 316
[3] METALATION AND ELECTROPHILIC SUBSTITUTION OF AMINE DERIVATIVES ADJACENT TO NITROGEN - ALPHA-METALLO AMINE SYNTHETIC EQUIVALENTS
BEAK, P
ZAJDEL, WJ
REITZ, DB
[J]. 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
BONNER, MP
THORNTON, ER
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) : 1299 - 1308
[5] SYNTHESIS OF R-LAUDANOSINE AND 9-R-O-METHYLFLAVINANTINE BY ASYMMETRIC ALKYLATION
GAWLEY, RE
SMITH, GA
[J]. 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
HOUSE, HO
EVANS, RA
TRAFICAN.DD
[J]. 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
HUBER, IMP
SEEBACH, D
[J]. HELVETICA CHIMICA ACTA, 1987, 70 (07) : 1944 - 1954

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