Stannane-free chemoselective hydrodehalogenation of 4-halotetrahydropyrans: Scope and application to natural product synthesis

Kok Ping Chan; Yvonne Hui Ling; Jocelyn Li Ting Chan; Teck Peng Loh

doi:10.1021/jo0624871

Stannane-free chemoselective hydrodehalogenation of 4-halotetrahydropyrans: Scope and application to natural product synthesis

Kok Ping Chan, Yvonne Hui Ling, Jocelyn Li Ting Chan, Teck Peng Loh

Nanyang Technological University

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

6 Scopus citations

Abstract

A stannane-free hydrodehalogenation of 4-halotetrahydropyran under very mild conditions has been developed. This methodology allows selective one-pot dehalogenation and/or debenzylation depending on the type of halide-substrate used. The applicability of this methodology is well demonstrated in the synthesis of a key intermediate toward the enantioselective synthesis of (+)-SCH 351448.

Original language	English
Pages (from-to)	2127-2132
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	72
Issue number	6
DOIs	https://doi.org/10.1021/jo0624871
State	Published - 16 Mar 2007
Externally published	Yes

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abstract = "A stannane-free hydrodehalogenation of 4-halotetrahydropyran under very mild conditions has been developed. This methodology allows selective one-pot dehalogenation and/or debenzylation depending on the type of halide-substrate used. The applicability of this methodology is well demonstrated in the synthesis of a key intermediate toward the enantioselective synthesis of (+)-SCH 351448.",

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AU - Chan, Jocelyn Li Ting

AU - Loh, Teck Peng

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AB - A stannane-free hydrodehalogenation of 4-halotetrahydropyran under very mild conditions has been developed. This methodology allows selective one-pot dehalogenation and/or debenzylation depending on the type of halide-substrate used. The applicability of this methodology is well demonstrated in the synthesis of a key intermediate toward the enantioselective synthesis of (+)-SCH 351448.

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Stannane-free chemoselective hydrodehalogenation of 4-halotetrahydropyrans: Scope and application to natural product synthesis

Abstract

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