Metalated nitriles: Chelation-controlled cyclizations to cis and trans hydrindanes and decalins

FF Fleming, VA Vu, BC Shook, M Rahman…

文献索引：Fleming, Fraser F.; Viet, Anh Vu; Shook, Brian C.; Rahman, Moshfiqur; Steward, Omar W. Journal of Organic Chemistry, 2007 , vol. 72, # 4 p. 1431 - 1436

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被引用次数: 19

摘要

Chelation provides a powerful means of stereocontrol in alkylations of metalated nitriles. Doubly deprotonating a series of cyclic β-hydroxynitriles triggers cyclizations that implicate metalated nitrile intermediates having configurations imposed by chelation with an adjacent, chiral lithium alkoxide. Identifying chelation as a general stereocontrol element explains several previously anomalous alkylations of metalated nitriles and provides a potential ...