ENANTIOSELECTIVE CONJUGATE ADDITION TO CYCLIC ENONES WITH SCALEMIC LITHIUM ORGANO(AMIDO)CUPRATES .4. RELATIONSHIP BETWEEN LIGAND STRUCTURE AND ENANTIOSELECTIVITY

被引：78

作者：

ROSSITER, BE

EGUCHI, M

MIAO, G

SWINGLE, NM

HERNANDEZ, AE

VICKERS, D

FLUCKIGER, E

PATTERSON, RG

REDDY, KV

机构：

[1] Department of Chemistry, Brigham Young University, Provo

来源：

TETRAHEDRON | 1993年 / 49卷 / 05期

关键词：

D O I：

10.1016/S0040-4020(01)86278-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Scalemic lithium amides derived from primary and secondary amines react with organocopper compounds in ether or dimethyl sulfide to form lithium organo(amido)cuprates capable of enantioselective conjugate addition to 2-cycloalkenones. The most successful heterocuprate, in which the chiral ligand is (S)-N-methyl-1-phenyl-2-(1-piperidinyl)ethanamine, (S)-MAPP, 13, reacts with cyclic enones to form products with up to 97% ee. Non-linear asymmetric induction was observed with the cuprate formed from ligand 13.

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页码：965 / 986

页数：22

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共 82 条

[61]

Schmalz H.-G., 1991, COMPREHENSIVE ORGANI, V4

[62] AMINOPHENYLETHANOLS AND RELATED COMPOUNDS [J].

SHAPIRO, SL ;

SOLOWAY, H ;

FREEDMAN, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (22) :6060-6064

[63] ASYMMETRIC CONJUGATE ADDITION OF GRIGNARD-REAGENTS IN THE PRESENCE OF TERTIARY-AMINES TO ALPHA,BETA-UNSATURATED AMIDES DERIVED FROM (S)-2-(1-HYDROXY-1-METHYLETHYL)PYRROLIDINE OR (S)-PROLINOL [J].

SOAI, K ;

MACHIDA, H ;

OOKAWA, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (08) :469-470

[64] ASYMMETRIC CONJUGATE ADDITION OF ORGANOMETALLIC REAGENTS IN THE PRESENCE OF TERTIARY-AMINES TO CHIRAL ALPHA,BETA-UNSATURATED AMIDO CARBOXYLIC-ACIDS - ADDITION ORDER OF REAGENTS AS AN UNPRECEDENTED FACTOR IN THE DETERMINATION OF THE SENSE OF ASYMMETRIC INDUCTION [J].

SOAI, K ;

OOKAWA, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (05) :759-764

[65] ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC TO ENONES USING CHIRAL BETA-AMINOALCOHOL AS CHIRAL CATALYST OR LIGAND [J].

SOAI, K ;

OKUDO, M ;

OKAMOTO, M .

TETRAHEDRON LETTERS, 1991, 32 (01) :95-96

[66] CATALYTIC ENANTIOSELECTIVE CONJUGATE ADDITION OF DIALKYLZINCS TO ALPHA,BETA-UNSATURATED KETONES USING NICKEL BROMIDE-N, N-DIBUTYLNOREPHEDRINE [J].

SOAI, K ;

HAYASAKA, T ;

UGAJIN, S ;

YOKOYAMA, S .

CHEMISTRY LETTERS, 1988, (09) :1571-1572

[67] ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE BETA-SUBSTITUTED KETONES BY HIGHLY ENANTIOSELECTIVE CATALYTIC CONJUGATE ADDITION OF DIALKYLZINC REAGENTS TO ENONES USING A CATALYST SYSTEM OF NICKEL(II)-CHIRAL LIGAND-ACHIRAL LIGAND IN ACETONITRILE TOLUENE [J].

SOAI, K ;

HAYASAKA, T ;

UGAJIN, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (08) :516-517

[68] Benzoylation of amino acids [J].

Steiger, RE .

JOURNAL OF ORGANIC CHEMISTRY, 1944, 9 (05) :396-400

[69] MOLECULAR-ORBITAL STUDY OF THE BONDING AND STRUCTURE OF ORGANOCUPRATES [J].

STEWART, KR ;

LEVER, JR ;

WHANGBO, MH .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (08) :1472-1474

[70] CHIRAL AMPLIFICATION IN THE SYNTHESIS OF (R)-MUSCONE BY CONJUGATE ADDITION OF CHIRAL ALKOXYDIMETHYLCUPRATE TO (E)-CYCLOPENTADEC-2-ENONE [J].

TANAKA, K ;

MATSUI, J ;

KAWABATA, Y ;

SUZUKI, H ;

WATANABE, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (22) :1632-1634

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