Stereoselective polysubstituted bicyclo[1.1.0]butane synthesis by rhodium-catalyzed kinetic resolution.

Authors

Xiaolong Zhang, Rongkai Wu, Zhaohong Liu, Ge Yin, Jiaqi Tang, Paramasivam Sivaguru, Xin Hong, Edward A Anderson, Xihe Bi

Published in

Science (New York, N.Y.). Pages eaeh6251. Sep 08, 2026. Epub Sep 08, 2026.

Abstract

Bicyclo[1.1.0]butanes (BCBs) are a distinctive class of strained small-ring carbocycles of growing importance in synthetic and medicinal chemistry. However, the enantioselective synthesis of polysubstituted BCBs remains a largely unsolved challenge. Herein, we report a general chemical platform for the stereoselective assembly of chiral or meso 1,2,3,4-tetrasubstituted BCBs from internal alkynes and carbenes via stepwise [2+1+1'] or one-pot [2+1+1] cycloaddition reactions, respectively. Successful execution of these transformations exploits the combination of triftosylhydrazones (carbene precursors) and chiral dirhodium catalysts. The sterically hindered catalyst Rh₂(R-3,5-diPheTPCP)₄ features a confined chiral microenvironment that enables exquisite discrimination between cyclopropene enantiomers, affording highly enantioenriched polysubstituted BCBs through kinetic resolution upon reaction with chiral rhodium carbenes. This chemistry operates under mild reaction conditions, employs readily available starting materials, and exhibits broad substrate scope.

PMID:
42709890
Bibliographic data and abstract were imported from PubMed on 09 Sep 2026.

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