The Chiral Auxiliary N-1-(1′-Naphthyl)ethyl-O-tert-butylhydroxylamine: A Chiral Weinreb Amide Equivalent

被引：14

作者：

Chernega, Alexander N. ^{[1
]}

Davies, Stephen G. ^{[1
]}

Goodwin, Christopher J. ^{[2
]}

Hepworth, David ^{[1
]}

Kurosawa, Wataru ^{[1
]}

Roberts, Paul M. ^{[1
]}

Thomson, James E. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] AstraZeneca R&D Charnwood, Proc R&D, Loughborough LE11 5RH, Leics, England

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 15期

关键词：

ASYMMETRIC-SYNTHESIS; SUPERQUAT ENAMIDES; ALPHA-ALKYLATION; CARBOXYLIC-ACIDS; KETONES; 5,5-DIMETHYL-4-ISO-PROPYLOXAZOLIDIN-2-ONE; N-ACYL-5,5-DIMETHYLOXAZOLIDIN-2-ONES; FUNCTIONALIZATION; PSEUDOEPHEDRINE; SUBSTITUTION;

D O I：

10.1021/ol901174t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine is readily prepared from N-hydroxyphthalimide in four steps, with resolution giving access to both enantiomers in >98% ee, on a multigram (>25 g) scale. Conversion to a range of N-acyl derivatives, followed by highly diastereoselective alkylation (>= 94% de) gives the corresponding chiral, 2-substituted derivatives as single diastereoisomers (>98% de) after chromatography. Reductive cleavage with LlAlH(4) allows direct access to chiral aldehydes, and treatment with MeLi gives chiral methyl ketones in excellent enantiopurity (>= 94% ee). The auxiliary can be recovered in >98% ee and recycled.

引用

页码：3254 / 3257

页数：4

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