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Enantioconvergent synthesis of (−)‐(S)‐ and (+)‐( R )‐2‐acetyl‐3,6‐dihydroxycyclohex‐2‐enone starting from rac ‐6‐hydroxy‐3‐methoxycyclohex‐2‐enone
Author(s) -
Zaitsev V.G.,
Mikhal'chuk A.L.
Publication year - 2001
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/chir.1066
Subject(s) - enone , chemistry , diastereomer , stereochemistry , organic chemistry
The synthesis of enantiomerically pure (−)‐( S )‐ and (+)‐( R )‐2‐acyl‐3,6‐dihydroxycyclohex‐2‐enone starting from diastereomerically pure N‐tosyl‐( S )‐proline esters 3‐methoxy‐6‐hydroxycyclohex‐2‐enone 1 is presented. An enantioconvergent synthesis of either (−)‐( S )‐ and (+)‐( R )‐2‐acyl‐3,6‐dihydroxycyclohex‐2‐enone starting with the racemic α‐ketol 1 through a conversion of (∼1:1) mixture of diastereomeric esters into one diastereomer by a repeated crystallization, followed by dimethylaminopyridine‐catalyzed equilibration as key steps is described. Chirality 13:488–492, 2001. © 2001 Wiley‐Liss, Inc.