Asymmetric synthesis of homoproline derivatives via Rh(I)-catalyzed hydrogenation using chiral bisphosphines as ligands

Yong Jian Zhang, Jung Hwan Park, Sang Gi Lee

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

It has been demonstrated for the first time that Rh(I)-catalyzed asymmetric hydrogenation of cyclic β-enamino acid derivatives 1 using chiral bisphosphines could be a highly efficient synthetic method for optically active homoproline derivatives. The enantioselectivity and conversion yield were largely dependent upon the chiral ligand. Using the Me-BDPMI forming a seven-membered metal chelate, the N-acetylated β-enamino acid methyl ester 1a was hydrogenated to give optically active homoproline derivative 2a with 100% conversion and 96% ee.

Original languageEnglish
Pages (from-to)2209-2212
Number of pages4
JournalTetrahedron Asymmetry
Volume15
Issue number14
DOIs
StatePublished - 26 Jul 2004

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