The importance of nitrogen substituents in chiral amino thiol ligands for the asymmetric addition of diethylzinc to aromatic aldehydes

被引：84

作者：

Anderson, JC ^{[1
]}

Harding, M ^{[1
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 03期

关键词：

D O I：

10.1039/a707937k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new series of N,S-chelate ligands derived from (S)-valine, which possess the capability of a stereogenic nitrogen donor atom, are catalysts for the addition of diethylzinc to aromatic aldehydes and gave the product secondary alcohols in up to 82% ee.

引用

页码：393 / 394

页数：2

共 16 条

[1] N-PHENYLATION OF AMINO-ACID DERIVATIVES [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J .

TETRAHEDRON LETTERS, 1989, 30 (08) :937-940

[2]

BOSNICH B, 1981, TOP STEREOCHEM, V12, P119

[3] PRACTICAL ENANTIOSELECTIVE DIELS-ALDER AND ALDOL REACTIONS USING A NEW CHIRAL CONTROLLER SYSTEM [J].

COREY, EJ ;

IMWINKELRIED, R ;

PIKUL, S ;

XIANG, YB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5493-5495

[4]

GURAM AS, 1995, ANGEW CHEM INT EDIT, V34, P1348, DOI 10.1002/anie.199513481

[5] SULFUR DERIVATIVES OF EPHEDRA ALKALOIDS - NEW AND HIGHLY EFFICIENT CHIRAL CATALYSTS [J].

HOF, RP ;

POELERT, MA ;

PEPER, NCMW ;

KELLOGG, RM .

TETRAHEDRON-ASYMMETRY, 1994, 5 (01) :31-34

[6]

KANG J, 1994, SYNLETT, P842

[7] The effects of sulfur substitution in chiral amino thiols on the enantioselective addition of organozinc reagents to aldehydes: A novel method for estimation of free energies of dimerization in monomer-dimer equilibria [J].

Kang, J ;

Kim, JB ;

Kim, JW ;

Lee, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (02) :189-194

[8] ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALPHA-BRANCHED ALDEHYDES [J].

KANG, J ;

LEE, JW ;

KIM, JI .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (17) :2009-2010

[9] A HIGHLY EFFICIENT AND GENERAL N-MONOMETHYLATION OF FUNCTIONALIZED PRIMARY AMINES VIA FORMYLATION BORANE METHYL SULFIDE REDUCTION [J].

KRISHNAMURTHY, S .

TETRAHEDRON LETTERS, 1982, 23 (33) :3315-3318

[10] PALLADIUM-CATALYZED SYNTHESIS OF ARYLAMINES FROM ARYL HALIDES - MECHANISTIC STUDIES LEAD TO COUPLING IN THE ABSENCE OF TIN REAGENTS [J].

LOUIE, J ;

HARTWIG, JF .

TETRAHEDRON LETTERS, 1995, 36 (21) :3609-3612

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