Highly enantioselective synthesis of chiral cyclic amino alcohols and conhydrine by ruthenium-catalyzed asymmetric hydrogenation.
A highly efficient enantio- and diastereoselective synthesis of chiral cis-beta-N-alkyl/arylamino cyclic alcohols has been realized by asymmetric hydrogenation of racemic alpha-amino cyclic ketones via DKR catalyzed by [RuCl(2)((S)-Xyl-SDP)((R,R)-DPEN)]. The enantioselectivities of the reaction were up to 99.9% ee with 99:1 cis-selectivities. A practical catalytic asymmetric synthesis of all four isomers of conhydrine was also developed.
Liu
Sheng
S
State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.
Xie
Jian-Hua
JH
Li
Wei
W
Kong
Wei-Ling
WL
Wang
Li-Xin
LX
Zhou
Qi-Lin
QL
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018652:Hemlock / Q000737:chemistry; D006865:Hydrogenation; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D000605:Amino Alcohols; D010880:Piperidines; C520251:alpha-conhydrine; D012428:Ruthenium