Sulfoxide-controlled S(N)2' displacements between cyanocuprates and epoxy vinyl sulfoxides.
J Org Chem
; 65(20): 6462-73, 2000 Oct 06.
Article
in En
| MEDLINE
| ID: mdl-11052089
ABSTRACT
Two short and convergent routes have been devised for the preparation of enantiomerically pure acyclic epoxy vinyl sulfoxides. These substrates undergo highly regio- and stereoselective S(N)2' displacements with lithium cyanocuprates to give alpha'-alkylated, gamma-oxygenated Z alpha,beta-unsaturated sulfoxides in moderate to good yields and with good to excellent diastereoselectivities. The absolute configuration of the newly formed carbon-carbon bond is primarily controlled by the chiral sulfur atom, which in a nonreinforcing situation can override the intrinsic anti tendency of the vinyl oxirane moiety and forces the cuprate to undergo syn addition. The hydroxy vinyl sulfoxide functionality of the resulting adducts should allow for subsequent asymmetric transformations thus enhancing the synthetic usefulness of this methodology.
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Collection:
01-internacional
Database:
MEDLINE
Main subject:
Organometallic Compounds
/
Sulfoxides
/
Vinyl Compounds
/
Copper
/
Epoxy Compounds
Language:
En
Journal:
J Org Chem
Year:
2000
Document type:
Article
Affiliation country:
Estados Unidos