TY - JOUR
T1 - Asymmetric reduction of imines with lithium butyl(hydro)dipinan-3α- yl-borate and related reagents
AU - Archer, J. F.
AU - Boyd, D. R.
AU - Jackson, W. R.
AU - Grundon, M. F.
AU - Khan, W. A.
PY - 1971/12/1
Y1 - 1971/12/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=37049128578&partnerID=8YFLogxK
U2 - 10.1039/J39710002560
DO - 10.1039/J39710002560
M3 - Article
AN - SCOPUS:37049128578
SP - 2560
EP - 2563
JO - Journal of the Chemical Society C: Organic Chemistry
JF - Journal of the Chemical Society C: Organic Chemistry
SN - 0022-4952
ER -