Asymmetric reduction of imines with lithium butyl(hydro)dipinan-3α- yl-borate and related reagents

J. F. Archer; D. R. Boyd; W. R. Jackson; M. F. Grundon; W. A. Khan

doi:10.1039/J39710002560

Asymmetric reduction of imines with lithium butyl(hydro)dipinan-3α- yl-borate and related reagents

J. F. Archer, D. R. Boyd, W. R. Jackson, M. F. Grundon, W. A. Khan

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

35 Citations (Scopus)

Abstract

Asymmetric reductions of a series of cyclic imines, 2-n-propyl-, 2-ethyl-, and 2-methyl-3,4,5,6-tetrahydropyridine, and also 3,4-dihydropapaverine with lithium butyl(hydro)dipinan-3α-ylborate and with the related methyl and phenyl compounds are described. A transition state which correlates the chirality of the reagents with that generated at the incipient chiral centre is proposed. Reductions with these reagents are shown to give amines of higher optical purity and opposite preferred chirality to those obtained by reductions with di- or tri-pinan-3α-yl-borane.

Original language	English
Pages (from-to)	2560-2563
Number of pages	4
Journal	Journal of the Chemical Society C: Organic Chemistry
DOIs	https://doi.org/10.1039/J39710002560
Publication status	Published - 1 Dec 1971
Externally published	Yes

Cite this

Archer, J. F., Boyd, D. R., Jackson, W. R., Grundon, M. F., & Khan, W. A. (1971). Asymmetric reduction of imines with lithium butyl(hydro)dipinan-3α- yl-borate and related reagents. Journal of the Chemical Society C: Organic Chemistry, 2560-2563. https://doi.org/10.1039/J39710002560

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AU - Boyd, D. R.

AU - Jackson, W. R.

AU - Grundon, M. F.

AU - Khan, W. A.

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10.1039/J39710002560

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