CHIRAL FORMAMIDINES - THE MECHANISM OF MONO-ALKYLATION AND DI-ALKYLATION LEADING TO CHIRAL, NON-RACEMIC TETRAHYDROISOQUINOLINES

被引：17

作者：

MEYERS, AI

WARMUS, JS

GONZALEZ, MA

GUILES, J

AKAHANE, A

机构：

[1] Department of Chemistry, Colorado State University, Fort Collins

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 40期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(91)80070-M

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The effect on facial selectivity and degree of stereoselectivity by varying the size of the chiral auxillary allows a mechanism for alkylation to be presented.

引用

页码：5509 / 5512

页数：4

共 12 条

[1] ASYMMETRIC-SYNTHESIS OF THE CORYNANTHEINE ALKALOIDS VIA AN INTRAMOLECULAR BLAISE REACTION - (-)-CORYNANTHEIDOL AND (-)-DIHYDROCORYNANTHEOL
BEARD, RL
MEYERS, AI
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) : 2091 - 2096
[2] CHIRAL DIPOLE-STABILIZED ANIONS - EXPERIMENT AND THEORY IN NONBENZYLIC SYSTEMS - 100-PERCENT STEREOSELECTIVE DEPROTONATION AND 2-ELECTRON VS SINGLE-ELECTRON TRANSFER IN THE CHEMISTRY OF LITHIUM AND COPPER PIPERIDINOOXAZOLINES
GAWLEY, RE
HART, GC
BARTOLOTTI, LJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01) : 175 - 181
[3] AN ASYMMETRIC-SYNTHESIS OF APORPHINE AND RELATED ALKALOIDS VIA CHIRAL FORMAMIDINES - (+)-GLAUCINE, (+)-HOMOGLAUCINE, AND (-)-8,9-DIDEMETHOXYTHALISOPAVINE
GOTTLIEB, L
MEYERS, AI
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) : 5659 - 5662
[4] QUANTITATIVE LINE-SHAPE ANALYSIS OF TEMPERATURE-DEPENDENT AND CONCENTRATION-DEPENDENT C-13-NMR SPECTRA OF LI-6-LABELED AND C-13-LABELED ORGANO-LITHIUM COMPOUNDS - KINETIC AND THERMODYNAMIC DATA FOR EXCHANGE PROCESSES IN DIBROMOMETHYLLITHIUM, (PHENYLTHIO)METHYLLITHIUM, AND BUTYLLITHIUM
HEINZER, J
OTH, JFM
SEEBACH, D
[J]. HELVETICA CHIMICA ACTA, 1985, 68 (07) : 1848 - 1862
[5] HIGHSMITH T, 1991, ASYMMETRIC SYNTHESIS
[6] A MECHANISTIC MODEL FOR ASYMMETRIC ALKYLATION OF CHIRAL DIPOLE STABILIZED ANIONS
LOEWE, MF
BOES, M
MEYERS, AI
[J]. TETRAHEDRON LETTERS, 1985, 26 (28) : 3295 - 3298
[7] ABSENCE OF AN ISOTOPE EFFECT ON THE METALATION OF CHIRAL FORMAMIDINES - THE MECHANISM OF ASYMMETRIC ALKYLATIONS LEADING TO CHIRAL AMINES
MEYERS, AI
DICKMAN, DA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) : 1263 - 1265
[8] MEYERS AI, 1991, TETRAHEDRON LETT
[9] NOYORI R, 1987, TETRAHEDRON LETT, V28, P4829
[10] DIASTEREOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL IMINIUM IONS - SYNTHESIS OF (S)-(+)-CRYPTOSTYLINE-I
POLNIASZEK, RP
DILLARD, LW
[J]. TETRAHEDRON LETTERS, 1990, 31 (06) : 797 - 800

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