Enantioselective Heck/Tsuji-Trost reaction of flexible vinylic halides with 1,3-dienes.

ABSTRACT: The enantioselective domino Heck/cross-coupling has emerged as a powerful tool in modern chemical synthesis for decades. Despite significant progress in relative rigid skeleton substrates, the implementation of asymmetric Heck/cross-coupling cascades of highly flexible haloalkene substrates remains a challenging and and long-standing goal. Here we report an efficient asymmetric domino Heck/Tsuji-Trost reaction of highly flexible vinylic halides with 1,3-dienes enabled by palladium catalysis. Specifically, the Heck insertion as stereodetermining step to form ƞ³ allyl palladium complex and in situ trapping with nucleophiles enable efficient Heck/etherification in a formal (4 + 2) cycloaddition manner. Engineering the Sadphos bearing androgynous non-C₂-symmetric chiral s

SUBMITTER: Zhang LZ 

PROVIDER: S-EPMC11754474 | biostudies-literature | 2025 Jan

REPOSITORIES: biostudies-literature