Alternative synthetic route to chiral N-substituted camphor-derived β-amino alcohols

Gin Ian Cheng; Chun Tin Shei; Kuangsen Sung

doi:10.1002/chir.20373

Alternative synthetic route to chiral N-substituted camphor-derived β-amino alcohols

Gin Ian Cheng, Chun Tin Shei, Kuangsen Sung

Department of Chemistry

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

6 Citations (Scopus)

Abstract

An alternative route from (1R)-(+)-camphor to chiral N-substituted camphor-derived β-amino alcohol (4b-e) consists of four steps with a total yield of 28%. N-Alkylation of camphor-derived β-amino alcohol (4a) involves condensation and hydride reduction in one pot without isolation of intermediates. Condensation of 4a with aldehydes or ketones generates a mixture of 1,3-oxazolidines (6) and imino-alcohols (7), which are reduced to 4b-e by NaBH₄.

Original language	English
Pages (from-to)	235-238
Number of pages	4
Journal	Chirality
Volume	19
Issue number	3
DOIs	https://doi.org/10.1002/chir.20373
Publication status	Published - 2007

All Science Journal Classification (ASJC) codes

Drug Discovery
Analytical Chemistry
Spectroscopy
Catalysis
Pharmacology
Organic Chemistry

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10.1002/chir.20373

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abstract = "An alternative route from (1R)-(+)-camphor to chiral N-substituted camphor-derived β-amino alcohol (4b-e) consists of four steps with a total yield of 28%. N-Alkylation of camphor-derived β-amino alcohol (4a) involves condensation and hydride reduction in one pot without isolation of intermediates. Condensation of 4a with aldehydes or ketones generates a mixture of 1,3-oxazolidines (6) and imino-alcohols (7), which are reduced to 4b-e by NaBH4.",

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Alternative synthetic route to chiral N-substituted camphor-derived β-amino alcohols

Abstract

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