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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A silver-catalyzed stereoselective domino cycloisomerization-vinylogous aldol reaction of -alkynylbenzaldehydes with 3-alkylidene oxindoles: an entry to functionalized isochromenes.
Chem Commun (Camb)
December 2020
Department of Chemistry, Indian Institute of Technology, Delhi, Hauz Khas, New Delhi-110016, India.
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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