160193-12-4Relevant academic research and scientific papers
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.
AuCl3/AgSbF6-catalyzed rapid epoxide to carbonyl rearrangement
Gudla, Vanajakshi,Balamurugan, Rengarajan
, p. 5243 - 5247 (2012/11/07)
An efficient epoxide to carbonyl rearrangement using catalytic AuCl 3/AgSbF6 has been presented. The reactions are fast and high yielding. β-Hydrogen migration takes place exclusively when hydrogen and methyl or substituted methyl groups are present at β-carbon of epoxide. When phenyl/acetyl/benzoyl and hydrogen are available at same carbon atom, migration of the former is preferred over the latter.
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.
Highly regio- and stereoselective rearrangement of epoxides to aldehydes catalyzed by high-valent metalloporphyrin complex, Cr(TPP)OTf
Suda, Kohji,Kikkawa, Taketoshi,Nakajima, Shin-Ichiro,Takanami, Toshikatsu
, p. 9554 - 9555 (2007/10/03)
Chromium(III) tetraphenylporphyrin triflate, Cr(TPP)OTf, works as an efficient and characteristic Lewis acid catalyst in the regio- and stereoselective rearrangement of epoxides to aldehydes. This Cr(TPP)OTf-catalyzed reaction is an operationally simple a
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.
Metalloporphyrin as an efficient catalyst in the regioselective isomerization of epoxides to carbonyl compounds
Takanami, Toshikatsu,Hirabe, Rina,Ueno, Masayoshi,Hino, Fumio,Suda, Kohji
, p. 1031 - 1032 (2007/10/03)
Regioselective ring-opening isomerization of epoxides to carbonyl compounds can effectively be catalyzed by iron (III) tetraphenylporphyrin, Fe(tpp)ClO4.
Baker's yeast-mediated reduction of α-hydroxy ketones and derivatives: The steric course of the biotransformation
Ferraboschi, Patrizia,Grisenti, Paride,Manzocchi, Ada,Santaniello, Enzo
, p. 10539 - 10548 (2007/10/02)
The results from the baker's yeast-mediated reduction of the acetates 3a- d and the methyl ethers 5a-d were compared with the same biotransformation which converts the α-hydroxy ketones 1a-d into the (R)-diols 2a-d (90- 98%ee); the acetates 3a-d afford the (S)-monoacetates 4a-d (72-94% ee) and the methyl ethers 5a-d are reduced to the (R)-monoethers 6a-d (64-76% ee).
