160193-12-4Relevant articles and documents
Rhodium-Catalyzed β-Dehydroborylation of Silyl Enol Ethers: Access to Highly Functionalized Enolates
Li, Jie,Li, Ruoling,Yang, Wen,Zhao, Pei,Zhao, Wanxiang
supporting information, p. 9580 - 9585 (2021/12/14)
An efficient rhodium-catalyzed β-dehydroborylation of aldehyde-derived silyl enol ethers (SEEs) with bis(pinacolato)diboron (B2pin2) is disclosed. The borylation reactions proceeded well with alkyl- and aryl-substituted SEEs, affording a wide array of valuable functionalized β-boryl silyl enolates with high efficiency and excellent stereoselectivity. Moreover, the borylated products, through versatile carbon–boron bond transformations, were readily converted into diverse synthetically useful molecules, including α-hydroxy ketones, functionalized SEEs, and gem-difunctionalized aldehydes.
β-fluoroamphetamines via the stereoselective synthesis of benzylic fluorides
Cresswell, Alexander J.,Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.,Tyte, Melloney J.
supporting information; experimental part, p. 2936 - 2939 (2010/09/10)
A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3-OEt 2 in CH2Cl2 at -20 -°C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective SN1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted β-fluoroamphetamines.
Chemocontrolled reduction of α-keto esters by hydrides: A possible solution for selective reduction of the ester function
Dalla,Catteau
, p. 6497 - 6510 (2007/10/03)
α-keto primary alcohols or α-silyloxy ketones have been obtained with a high level of selectivity from enolic α-keto esters in two steps, with the reduction of the α-silyloxy α,β-unsaturated ester by LiAlH4 as the key step. The methodology developed in this work represents a 'reversed' chemoselective reduction of the ester group instead of the keto of an enolic α-keto ester due to a one-pot sequential ester reduction-desilylation or silyl migration process.
