Enantioselective synthesis of cyclic enol ethers and all-carbon quaternary stereogenic centers through catalytic asymmetric ring-closing metathesis

Journal of the American Chemical Society

Volumn 128, Issue 15, 2006, Pages 5153-5157

  Lee, Ai Lan ^a   Malcolmson, Steven J ^a   Puglisi, Alessandra ^a   Schrock, Richard R ^b   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSIS; PHASE TRANSITIONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CYCLIC ENOL ETHERS; PHOSPHINE LIGAND; QUATERNARY STEREOGENIC CENTERS; RING-CLOSING METATHESIS;

ETHERS;

ALKENE; ALKYLIDENE; CARBON; CYCLIC ENOL ETHER; ETHER DERIVATIVE; LIGAND; MOLYBDENUM; PHOSPHINE; RUBIDIUM; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC RING CLOSING METATHESIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; MECHANISTIC MODEL; MODEL; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS; TRANSFORMATION REACTION;

ALKENES; CATALYSIS; CYCLIZATION; CYCLOPARAFFINS; ETHERS, CYCLIC; MODELS, MOLECULAR; STEREOISOMERISM;

EID: 33646142091     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja058428r     Document Type: Article

References (41)

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34. See the Supporting Information for details.
35. Typically, in catalytic asymmetric desymmetrization reactions involving trienes or tetraenes, high enantioselectivities are attained if initiation (formation of the M=C bond) occurs at the central unsaturation site followed by enantioselective ring closure (e.g., reactions in Tables 2 and 4). As a result, reactions of all-terminal olefins typically proceed with low enantioselectivity. An example is illustrated below: (Equation Presented)
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