Regio‐ and Enantioselective Synthesis of Sulfone‐Bearing Quaternary Carbon Stereocenters by Pd‐Catalyzed Allylic Substitution
Abstract
Chiral sulfones are of great importance in medicinal chemistry and chemical synthesis. Efficient methods for preparing enantiomerically enriched sulfone‐containing molecules can therefore be of significant value; such methods, however, are uncommon. Herein, we report the first general palladium‐catalyzed sulfonylation of vinyl cyclic carbonates with sodium sulfinates. A series of enantiomerically enriched tertiary allylic sulfones were synthesized in good yields with excellent enantiomeric ratios. Both aliphatic‐ and aryl‐substituted vinyl cyclic carbonates are suitable reactants with excellent results. This reaction features broad substrates scope, readily available starting materials, excellent regio‐ and enantioselectivity, and synthesis of sulfone‐bearing quaternary carbon stereocenters. Through the sulfonylation of geranyl derived cyclic carbonate 1 h, we achieve the formal total synthesis of (+)‐agelasidine A.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Nov 14, 2019
- Source ID
- 10.1002/anie.201910378
Entities
People
- Ajmal Khan
- Depeng Zhao
- Heng Zhao
- Meina Zhang
- Shahid Ullah Khan
Organizations
- Office of Naval Research
- Sun Yat-sen University
- Xi'an Jiaotong University