In 2017,Park, Jinyoung; Choi, Seoyoung; Lee, Yeosan; Cho, Seung Hwan published ãChemo- and stereoselective crotylation of aldehydes and cyclic aldimines with allylic gem-diboronate esterã?Organic Letters published the findings.Reference of Bis[(pinacolato)boryl]methane The information in the text is summarized as follows:
We report a highly chemo- and stereoselective crotylation of aldehydes and cyclic aldimines with allylic-gem-diboronate ester (E)-MeCH:CHCH(Bpin)2 (2a), which as a new type of organoboron reagent. Crotylation of aldehydes R1CHO with 2a affords cyclic vinylboronates I (4a-q; R1 = aryl, 2-furyl, 2-thienyl, PhCH:CH, PhCH2CH2), while cyclic aromatic aldimines R2C6H3-1,2-OSO2N:CH gave vinylboronates II (6a-l; R2 = H, halo, Me, MeO, benzo, OCH2O) in excellent stereoselectivity, forming anti-5,6-disubstituted oxaborinin-2-ols or (E)-δ-boryl-anti-homoallylic amines in high efficiency. The reaction shows a wide range of substrate scope and excellent functional group tolerance. The synthetic applications of the obtained products, including stereospecific C-C, C-O, and C-Cl bond formation, are also demonstrated. After reading the article, we found that the author used Bis[(pinacolato)boryl]methane(cas: 78782-17-9Reference of Bis[(pinacolato)boryl]methane)
Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds are versatile intermediates and as such are some of the most important classes of reagents in modern organic chemistry. This stems from their ease of preparation combined with their ability to undergo a broad range of chemical transformations.Reference of Bis[(pinacolato)boryl]methane
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