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Asymmetric synthesis of hydroxylated pyrrolizidine, indolizidine, and (+)‐α‐conhydrine via ruthenium‐catalyzed hydrogenation
Author(s) -
Guerreiro Patricio,
RatovelomananaVidal Virginie,
Genêt JeanPierre
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(2000)12:5/6<408::aid-chir20>3.0.co;2-g
Subject(s) - chemistry , indolizidine , pyrrolizidine , ruthenium , catalysis , asymmetric hydrogenation , enantioselective synthesis , organic chemistry , combinatorial chemistry , stereochemistry , alkaloid
The enantioselective ruthenium promoted hydrogenation of β‐keto ester, derived from ( S )‐ or ( R )‐proline and ( S )‐pipecolic acid, provided a new efficient route to hydroxylated pyrrolizidine or indolizidine ring systems in diastereomeric excesses up to 99%. A practical synthesis of (+)‐α‐conhydrine is also reported. Chirality 12:408–410, 2000. © 2000 Wiley‐Liss, Inc.