Gold(I)-Catalyzed Stereoselective Cyclization of 1,3-Enyne Aldehydes by 1,3-Acyloxy Migration/Nazarov/Aldol Cascade
2019-06-10T18:18:52Z (GMT)
by
Stereoselective synthesis of
bicyclo[3.3.0]octenones from chiral 1,3 enyne aldehydes bearing propargylic
acetates is described. The method is based on a Au(I)-catalyzed domino sequence
with concomitant transfer of chirality involving 1,3-acyloxy migration followed
by Nazarov cyclization and an unprecedented aldol addition. The method furnishes
densely functionalized bicyclic structures in high yields, up to 97% ee, and
good diastereoselectivity.
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