A silver-catalyzed stereoselective domino cycloisomerization-vinylogous aldol reaction of ortho -alkynylbenzaldehydes with 3-alkylidene oxindoles: an entry to functionalized isochromenes

Chemical Communications : Chem Comm
Krishna KumarRavi P Singh

Abstract

A silver tetrafluoroborate catalyzed domino cycloisomerization-vinylogous aldol addition sequence on a multifunctional substrate such as ortho-alkynylbenzaldehydes yielding functionalized 1H-isochromenes in a single step with high yield and excellent diastereoselectivity (>19 : 1) is described. The reaction was well tolerated by alkyl, aryl, and unsubstituted alkynylbenzaldehydes, and furnished selective 6-endo-dig adducts exclusively without loss in the regio- as well as diastereoselectivity.

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Citations

Nov 27, 2021·Organic & Biomolecular Chemistry·Tzu-Hsuan KuanDuen-Ren Hou

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Methods Mentioned

BETA
X-ray

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