148259-45-4Relevant articles and documents
tert-Butyldimethylsilyldihalomethyllithium as a dihalomethylene dianion synthon. 1,3-Rearrangement and 1,4-rearrangement of silyl group from carbon to oxide
Shinokubo, Hiroshi,Miura, Katsukiyo,Oshima, Koichiro,Utimoto, Kiitiro
, p. 503 - 514 (2007/10/03)
One-pot synthesis of R1CH(OSiMe2-t-Bu)CX2CH(OH)R2 (X = Cl, Br) by successive addition of two different aldehydes (R1CHO and R2CHO) has been achieved starting from tert-butyldimethylsilyldihalomethyllithium. Treatment of a THF solution of the title carbanion (X = Cl) with p-MeOC6H4CHO or n-BuCHO followed by an addition of HMPA and benzaldehyde gave the corresponding 1,3-diol monosilyl ether in 83% or 45% yield, respectively. The use of oxirane in place of aldehyde as the first electrophile followed by addition of benzaldehyde provided 1,4-diol monosilyl ether.