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

Yong Jian Zhang; Jung Hwan Park; Sang Gi Lee

doi:10.1016/j.tetasy.2004.04.014

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

Yong Jian Zhang, Jung Hwan Park, Sang Gi Lee

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

31 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 language	English
Pages (from-to)	2209-2212
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	15
Issue number	14
DOIs	https://doi.org/10.1016/j.tetasy.2004.04.014
State	Published - 26 Jul 2004

Bibliographical note

Funding Information:
This work was supported by a Korea National Center for Cleaner Production, a National Research Laboratory Program from MOST, a Center for Molecular Design and Synthesis at KAIST and a KIST. We would also like to thank Professor K. M. Kim for X-ray analysis and Leadgene Co. Ltd who generously supplied the cyclic β-enamino acid derivatives.

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

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.",

author = "Zhang, {Yong Jian} and Park, {Jung Hwan} and Lee, {Sang Gi}",

note = "Funding Information: This work was supported by a Korea National Center for Cleaner Production, a National Research Laboratory Program from MOST, a Center for Molecular Design and Synthesis at KAIST and a KIST. We would also like to thank Professor K. M. Kim for X-ray analysis and Leadgene Co. Ltd who generously supplied the cyclic β-enamino acid derivatives.",

year = "2004",

month = jul,

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doi = "10.1016/j.tetasy.2004.04.014",

language = "English",

volume = "15",

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journal = "Tetrahedron Asymmetry",

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T1 - Asymmetric synthesis of homoproline derivatives via Rh(I)-catalyzed hydrogenation using chiral bisphosphines as ligands

AU - Zhang, Yong Jian

AU - Park, Jung Hwan

AU - Lee, Sang Gi

N1 - Funding Information: This work was supported by a Korea National Center for Cleaner Production, a National Research Laboratory Program from MOST, a Center for Molecular Design and Synthesis at KAIST and a KIST. We would also like to thank Professor K. M. Kim for X-ray analysis and Leadgene Co. Ltd who generously supplied the cyclic β-enamino acid derivatives.

PY - 2004/7/26

Y1 - 2004/7/26

N2 - 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.

AB - 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.

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U2 - 10.1016/j.tetasy.2004.04.014

DO - 10.1016/j.tetasy.2004.04.014

M3 - Article

AN - SCOPUS:3843097462

SN - 0957-4166

VL - 15

SP - 2209

EP - 2212

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 14

ER -

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

Abstract

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