Chemistry of Heterocyclic Compounds p. 86 - 88 (1980)
Update date:2022-08-05
Topics:
Grishina, G.V.
Potapov, V.M.
Gudasheva, T.A.
A new method for the asymmetric synthesis of cycloalkano-2,3-piperid-4-ols by the reaction of a number of chiral enamino ketones with sodium borohydride is proposed.It is shown that the reduction proceeds via 1,4-hydride addition and leads to the formation of primarily one diastereomeric pair of cycloalkano-2,3-popiridols and their dehydration products.The asymmetric synthesis was confirmed by the production of optically active nitrogen-unsubstituted cycloalkano-2,3-piperid-4-ols when the chiral substituent was removed.
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Doi:10.1016/S0040-4039(00)71182-8
(1980)Doi:10.1039/b404425h
(2004)Doi:10.1016/j.bmc.2004.05.038
(2004)Doi:10.1002/chem.201504515
(2016)Doi:10.1055/s-1997-739
(1997)Doi:10.1021/jm049968m
(2004)
