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Enantioselective Aldol Reaction of α ‐Ketoester and Cyclopentaone Catalyzed by L ‐Proline
Author(s) -
Xiang Jiming,
Li Baolin
Publication year - 2010
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201090122
Subject(s) - chemistry , enantioselective synthesis , aldol reaction , stereocenter , stereoselectivity , aldol condensation , organic chemistry , cyclopentanone , catalysis , stereochemistry
A concise and enantioselective synthesis of ( S )‐ethyl 2‐cyclopentyl‐2‐hydroxy‐2‐arylacetate, a key intermediate for the muscarinic receptor, is reported. The tertiary stereogenic center was constructed with good stereoselectivity through the L‐ proline‐catalyzed direct asymmetric aldol reaction of ethyl arylglyoxylate and cyclopentanone. The carbonyl of the condensation product was reduced using a modified Clemmensen reaction which provided an easier workup and was more environmentally acceptable. The enantioselectivity of the aldol reactions was between 58.3%–93.2%, which means that the stereoselective is efficient in controlling configuration of reaction product.