ISSN:
0947-6539
Keywords:
asymmetric syntheses
;
enol ethers
;
Fischer carbenes
;
Michael additions
;
syn diastereoselectivity
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Michael addition reactions of ketone and ester lithium enolates to optically active Fischer vinylcarbene complexes derived from (-)-8-phenylmenthol take place with high syn selectivity and high levels of asymmetric induction. The initial Michael adducts can be further elaborated through diastereoselective addition of organometallic reagents to ketones and aldol reactions. Removal of the metal fragment and chiral auxiliary group leads to cyclic enol ethers with three or five contiguous stereogenic centers and of high enantiomeric purity.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.19950010407
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