Premium
Synthesis of D ‐(+)‐Biotin through Selective Ring Closure of N ‐Acyliminium Silyl Enol Ethers
Author(s) -
Moolenaar Marinus J.,
Speckamp W. Nico,
Hiemstra Henk,
Poetsch Eike,
Casutt Michael
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199523911
Subject(s) - stereocenter , silylation , total synthesis , ring (chemistry) , enol , chemistry , biotin , stereochemistry , silyl enol ether , closure (psychology) , center (category theory) , silyl ether , lewis acids and bases , transformation (genetics) , enantioselective synthesis , catalysis , organic chemistry , crystallography , biochemistry , economics , market economy , gene
Irrespective of the geometry of the double bond the configuration of the newly formed chiral center is established by the existing adjacent stereogenic center in the Lewis acid catalyzed cyclization of the N ‐acyliminium silyl enol ether intermediate 1 . This step is the key transformation in a new, concise total synthesis of D ‐( + )‐biotin. R protecting group.