Stereocontrolled oxidative addition of zerovalent molybdenum to enantiomerically pure allylic acetates with either inversion or retention at the stereogenic center

Journal of the American Chemical Society

Volumn 118, Issue 4, 1996, Pages 897-898

  Ward, Yancey D ^a,b   Villanueva, Lawrence A ^a   Allred, Gary D ^a   Liebeskind, Lanny S ^a  

^a EMORY UNIVERSITY   (United States)

^b BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000596906     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952938b     Document Type: Article

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38. One referee suggested that dihydropyranones 3(S) and 3(R), while not sterically biased, are conformationally biased. A conformational bias would be mechanistically significant only if the more abundant half-chair (pseudoequatorial OAc) and the less abundant half-chair (pseudoaxial OAc) each react selectively under different reaction conditions. To account for the observed oxidative addition stereoselectivities, oxidative addition at low Mo(0) concentration could proceed selectively ryn to the pseudoaxial allylic acetate, in which case at high effective Mo(0) concentration oxidative addition must proceed anti to the pseudoequatorial OAc group, possibly through a molybdenum aggregate.