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Catalytic asymmetric borylative aldol reaction of 5,6-dihydro-2H-pyran-2-one and ketones

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Abstract A copper(I)-catalyzed asymmetric borylative aldol reaction of 5,6-dihydro-2H-pyran-2-one and simple ketones (including aromatic ketones and an aliphatic ketone) was disclosed, which afforded a series of chiral diols after an… Click to show full abstract

Abstract A copper(I)-catalyzed asymmetric borylative aldol reaction of 5,6-dihydro-2H-pyran-2-one and simple ketones (including aromatic ketones and an aliphatic ketone) was disclosed, which afforded a series of chiral diols after an oxidative work-up in moderate yields with moderate to high diastereoselectivity and excellent enantioselectivity. The lactone moiety was easily opened with methanol to generate a chiral triol in moderate yield.

Keywords: aldol reaction; dihydro pyran; asymmetric borylative; borylative aldol; reaction dihydro; pyran one

Journal Title: Tetrahedron
Year Published: 2019

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