Copper-catalyzed enantioselective diyne cyclization via C(sp 2 )-O bond cleavage

The functionalization of etheric C-O bonds C-O bond cleavage is an attractive strategy for the construction of C-C and C-X bonds in organic synthesis. However, these reactions mainly involve C(sp )-O bond cleavage, and a catalyst-controlled highly enantioselective version is extremely challenging. H...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2023-03, Vol.14 (13), p.3493-3500
Main Authors: Zhou, Ji-Jia, Meng, Ya-Nan, Liu, Li-Gao, Liu, Yi-Xi, Xu, Zhou, Lu, Xin, Zhou, Bo, Ye, Long-Wu
Format: Article
Language:English
Subjects:
Chemical synthesis
Chemistry
Cleavage
Copper
Enantiomers
Pyrroles
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Summary:The functionalization of etheric C-O bonds C-O bond cleavage is an attractive strategy for the construction of C-C and C-X bonds in organic synthesis. However, these reactions mainly involve C(sp )-O bond cleavage, and a catalyst-controlled highly enantioselective version is extremely challenging. Here, we report a copper-catalyzed asymmetric cascade cyclization C(sp )-O bond cleavage, allowing the divergent and atom-economic synthesis of a range of chromeno[3,4- ]pyrroles bearing a triaryl oxa-quaternary carbon stereocenter in high yields and enantioselectivities. Importantly, this protocol not only represents the first [1,2]-Stevens-type rearrangement C(sp )-O bond cleavage, but also constitutes the first example of [1,2]-aryl migration reactions vinyl cations.
ISSN:2041-6520
2041-6539
DOI:10.1039/d2sc06152j