A convenient preparation of enantiomerically pure (+)-(1R,2R)-and (-)-(1S,2S)-1,2-diamino-1,2-diphenylethanes

被引：23

作者：

Braddock, D. Christopher ^{[1
]}

Redmond, Joanna M.

Hermitage, Stephen A.

White, Andrew J. P.

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Synth Sect, Dept Chem, London SW7 2AZ, England

[2] GlaxoSmithKline Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 7-8期

关键词：

iso-amarine; amines; asymmetric synthesis; enantiomeric resolution; fractional crystallisation;

D O I：

10.1002/adsc.200505440

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A gram-scale preparation of (1S,2S)- and (1R,2R)-1,2-diamino-1,2-diphenylethanes, (1S,2S)-1 and (IR,2R)-1, is reported via (+/-)-iso-amarine 4. Strategically, the activation of (+/-)-iso-amarine 4 for hydrolysis to the required diamines and enantiomeric resolution is achieved simultaneously by formation of two separable diastereoisomeric N-acylamidines 5 and 6 derived from direct DCC-mediated coupling of (+/-)-iso-amarine 4 with (R)-acetylmandelic acid. iso-Amarine 4 is conveniently obtained from amarine 3, and a one-pot synthesis of the latter is reported from benzaldehyde and hexamethyldisilazane as catalysed by benzoic acid.

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页码：911 / 916

页数：6

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