Stereocontrol in the synthesis of cyclic amino acids: a new ligand for directed hydrogenation through hydrogen bonding

Vasudeva Rao Gandi; Bao Nguyen Do Doan; Sivarajan Kasinathan; Roderick W. Bates

doi:10.1039/C9OB00003H

Stereocontrol in the synthesis of cyclic amino acids: a new ligand for directed hydrogenation through hydrogen bonding

Vasudeva Rao Gandi, Bao Nguyen Do Doan, Sivarajan Kasinathan, Roderick W. Bates^*

^*Corresponding author for this work

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

5 Citations (Scopus)

Abstract

A system for the directed hydrogenation of nitrogen heterocycles is described in which hydrogen is delivered cis to a hydroxymethyl group by a rhodium catalyst with a simple phosphine ligand. The chemistry is applied to the synthesis of the hygric acid moiety of lincomycin and the pipecolic acid moiety of Argatroban. A series of control experiments indicate that the stereoselectivity is a result of a combination of both coordination and hydrogen bonding.

Original language	English
Pages (from-to)	2753-2758
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	17
Issue number	10
DOIs	https://doi.org/10.1039/C9OB00003H
Publication status	Published - 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A system for the directed hydrogenation of nitrogen heterocycles is described in which hydrogen is delivered cis to a hydroxymethyl group by a rhodium catalyst with a simple phosphine ligand. The chemistry is applied to the synthesis of the hygric acid moiety of lincomycin and the pipecolic acid moiety of Argatroban. A series of control experiments indicate that the stereoselectivity is a result of a combination of both coordination and hydrogen bonding.",

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AU - Gandi, Vasudeva Rao

AU - Doan, Bao Nguyen Do

AU - Kasinathan, Sivarajan

AU - Bates, Roderick W.

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PY - 2019

Y1 - 2019

N2 - A system for the directed hydrogenation of nitrogen heterocycles is described in which hydrogen is delivered cis to a hydroxymethyl group by a rhodium catalyst with a simple phosphine ligand. The chemistry is applied to the synthesis of the hygric acid moiety of lincomycin and the pipecolic acid moiety of Argatroban. A series of control experiments indicate that the stereoselectivity is a result of a combination of both coordination and hydrogen bonding.

AB - A system for the directed hydrogenation of nitrogen heterocycles is described in which hydrogen is delivered cis to a hydroxymethyl group by a rhodium catalyst with a simple phosphine ligand. The chemistry is applied to the synthesis of the hygric acid moiety of lincomycin and the pipecolic acid moiety of Argatroban. A series of control experiments indicate that the stereoselectivity is a result of a combination of both coordination and hydrogen bonding.

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Stereocontrol in the synthesis of cyclic amino acids: a new ligand for directed hydrogenation through hydrogen bonding

Abstract

Bibliographical note

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