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Dynamic Kinetic Resolution of Primary Alcohols with an Unfunctionalized Stereogenic Center in the β‐Position
Author(s) -
Strübing Dirk,
Krumlinde Patrik,
Piera Julio,
Bäckvall JanE.
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700222
Subject(s) - chemistry , kinetic resolution , racemization , stereocenter , ruthenium , aldehyde , alcohol , catalysis , organic chemistry , dehydrogenation , primary (astronomy) , enantioselective synthesis , physics , astronomy
Primary alcohols with an unfunctionalized stereogenic center in the β‐position undergo an enzyme‐ and metal‐catalyzed dynamic kinetic resolution (DKR). The in situ racemization of the primary alcohol, required for the DKR, takes place via : (i) ruthenium‐catalyzed dehydrogenation of the alcohol, (ii) enolization of the aldehyde formed, and (iii) ruthenium‐catalyzed readdition of hydrogen to the aldehyde. The present method widens the scope of metal‐ and enzyme‐catalyzed DKR, which has so far been limited to α‐chiral alcohol and amine derivatives.