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Aziridinyl ketones XVII. The hydrogenation of 2‐phenyl‐3‐aroylaziridines to aziridinylcarbinols
Author(s) -
Wall Donald K.,
Imbach JeanLouis,
Pohland Albert E.,
Badger Robert C.,
Cromwell Norman H.
Publication year - 1968
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570050113
Subject(s) - chemistry , lithium diisopropylamide , sodium borohydride , ketone , lithium (medication) , catalytic hydrogenation , aziridine , medicinal chemistry , aluminum hydride , catalysis , ring (chemistry) , borohydride , hydride , organic chemistry , hydrogen , ion , medicine , methoxide , deprotonation , endocrinology
The sodium borohydride reduction of both cis and trans ‐1‐cyclohexyl‐2‐phenyl‐3‐aroylaziridines provides in each case the corresponding carbinol as a mixture of the two possible diastereoisomeric racemates, whereas reduction of these ketones with lithium aluminum hydride or with lithium diisopropylamide provides only the racemate resulting from attack on the carbonyl group from the least hindered side. Catalytic hydrogenation of a cis aziridinyl ketone cleaved the aziridine ring and provided an amino carbinol.