Organic Letters
Organic Letters
3 years ago

Chemo- and Stereoselective Crotylation of Aldehydes and Cyclic Aldimines with Allylic gem-Diboronate Ester

Chemo- and Stereoselective Crotylation of Aldehydes and Cyclic Aldimines with Allylic gem-Diboronate Ester
Seoyoung Choi, Jinyoung Park, Yeosan Lee, Seung Hwan Cho
We report a highly chemo- and stereoselective crotylation of aldehydes and cyclic aldimines with allylic-gem-diboronate ester as a new type of organoboron reagent. The allylic-gem-diboronate ester undergoes the crotylation with aldehydes and cyclic aldimines 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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01821

DOI: 10.1021/acs.orglett.7b01821

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