Generation of ketone dilithio α,β-dianions and their reactions with electrophiles
摘要:
Ketone dilithio alpha,beta- and alpha,beta'-dianions can be generated by a tin-lithium exchange reaction of the lithium enolate of beta-tributyltin substituted ketones. A chelation-aided approach, which employs beta-dichlorobutyltin substituted ketones and n-BuLi, is also useful for the generation of ketone alpha,beta-dianions having the Z-geometry at the alkene. The generated dianions can be transformed into substituted ketones by reaction with various carbon electrophiles. (c) 2005 Elsevier Ltd. All rights reserved.
Ketone dilithio alpha,beta- and alpha,beta'-dianions can be generated by a tin-lithium exchange reaction of the lithium enolate of beta-tributyltin substituted ketones. A chelation-aided approach, which employs beta-dichlorobutyltin substituted ketones and n-BuLi, is also useful for the generation of ketone alpha,beta-dianions having the Z-geometry at the alkene. The generated dianions can be transformed into substituted ketones by reaction with various carbon electrophiles. (c) 2005 Elsevier Ltd. All rights reserved.
Hannaby, Malcolm; Judson, Philip; Warren, Stuart, Journal of the Chemical Society. Perkin transactions I, 1992, # 20, p. 2609 - 2614