Tetrahedron

The crucial role of the nitrogen substituent in the desymmetrisation of cyclic meso-imides using B-Me and B-OMe oxazaborolidine catalysts

MD Barker, RA Dixon, S Jones, BJ Marsh

文献索引：Barker, Mike D.; Dixon, Rachel A.; Jones, Simon; Marsh, Barrie J. Tetrahedron, 2006 , vol. 62, # 50 p. 11663 - 11669

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被引用次数: 12

摘要

Various cyclic meso-imides have been desymmetrised via enantioselective reduction using two chiral oxazaborolidine catalysts derived from (1R, 2S)-cis-1-amino-indan-2-ol followed by the reduction of the hydroxylactam product to give the γ-lactam. The enantiomeric excesses were shown to be 27–99% by chiral HPLC and chiral GC of the γ-lactam products with the nitrogen substituent playing a pivotal role in determining yield and selectivity.