125138-00-3Relevant academic research and scientific papers
Transition-Metal-Free Formylation of Allylzinc Reagents Leading to α-Quaternary Aldehydes
Haraguchi, Ryosuke,Kusakabe, Akinori,Mizutani, Nakaba,Fukuzawa, Shin-Ichi
supporting information, p. 1613 - 1616 (2018/03/23)
The first example of formylation of allylzinc reagents using S-phenyl thioformate is presented. The reaction proceeded under mild conditions without any transition-metal catalyst, forming quaternary carbon centers with reactive functionalities, such as formyl and vinyl groups. Moreover, Barbier-type formylation of an allylic bromide with a sterically demanding thioformate was achieved. As a preliminary result, asymmetric formylation was conducted using a menthol-derived chiral thioformate.
Studies toward the generation of functionalized quaternary carbon centers relying on wittig and wittig-still allylic ether anionic transpositions
Hanessian, Stephen,Dorich, Stephane,Chattopadhyay, Amit Kumar,Bueschleb, Martin
, p. 8915 - 8921 (2013/09/24)
Although the [2,3]-Wittig and Wittig-Still rearrangements have long been known, their application in the generation of quaternary carbon centers in carbocyclic ring systems is sparse. Model studies utilizing this strategy and possible mechanisms are discussed herein. Unprecedented examples of an α-elimination pathway from stannylmethyl allyl ethers as a major undesired product in some Wittig-Still rearrangements are reported.
One-Pot Conversions of (Silylmethyl)cyclopropanes to Homoallylic Alcohols and 1,4-Diols Based on Haloborane-Induced Ring Opening
Ryu, Ilhyong,Hirai, Akira,Suzuki, Haruhisa,Sonoda, Noboru,Murai, Shinji
, p. 1409 - 1410 (2007/10/02)
The reactions of (silylmethyl)cyclopropanes with haloboranes, such as BBr3 and BHBr2, result in desilylative ring opening to give homoallylboranes and boracyclopentanes, respectively.Coupled with subsequent oxidation procedure, these reactions provide ready access to homoallylic alcohols and 1,4-diols.
