Desymmetrization of Cyclic Sulfonimidamides by Asymmetric Allylation

Author:

Gutierrez David A.1,Toth‐Williams Garrett1,Laconsay Croix J.2,Yasuda Michael1,Fettinger James C.1,Di Maso Michael J.3,Shaw Jared T.1ORCID

Affiliation:

1. Department of Chemistry University of California, Davis One Shields Ave. Davis California 95616 United States

2. Department of Chemistry University of Houston 3585 Cullen Blvd. Houston Texas 77004 United States

3. Department of Process Research and Development Merck & Co., Inc. Rahway, New Jersey 07065 United States

Abstract

AbstractHerein we report the first transition metal‐catalyzed approach to the enantioenriched synthesis of cyclic sulfonimidamides relying on commercially available palladium catalysts and ligands. High‐throughput experimentation (HTE) was employed to identify the optimal catalyst system and solvent. The method is applied to a variety of saturated and unsaturated rings and exhibits the highest selectivity for 2‐substituted allyl electrophiles. The products are further elaborated to complex, tricyclic scaffolds. DFT experiments presented herein highlight the key ligand substrate interactions leading to the high levels of enantioselectivity.

Funder

National Science Foundation

Publisher

Wiley

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