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Org Lett. 2008 Mar 20;10(6):1259-62. doi: 10.1021/ol8001514. Epub 2008 Feb 15.

Remarkable salt effect on In-mediated allylation of N-tert-butanesulfinyl imines in aqueous media: highly practical asymmetric synthesis of chiral homoallylic amines and isoindolinones.

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1
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.

Abstract

A highly practical and efficient asymmetric synthesis of chiral homoallylic amines by In-mediated allylation of chiral N-tert-butanesulfinyl imines in aqueous media at room temperature was developed. With 2-formylbenzoate imine substrates, the method allows the highly enantioselective achievement of a variety of pharmacologically important 3-allyl isoindolinone compounds.

PMID:
18275212
DOI:
10.1021/ol8001514
[Indexed for MEDLINE]
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