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Catalytic Enantioselective Synthesis of Highly Functionalized Pentafluorosulfanylated Pyrrolidines
Author(s) -
Zhao Qun,
Vuong Thi Minh Ha,
Bai XingFen,
Pannecoucke Xavier,
Xu LiWen,
Bouillon JeanPhilippe,
Jubault Philippe
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201706167
Subject(s) - enantioselective synthesis , catalysis , combinatorial chemistry , chemistry , organic chemistry
The first catalytic asymmetric synthesis of highly functionalized pentafluorosulfanylated pyrrolidines is described. The method, based on a 1,3‐dipolar cycloaddition reaction of aryl and heteroaryl‐substituted glycine Schiff bases with pentafluorosulfanyl acrylic esters, gave access to a broad range of pyrrolidines bearing aryl, naphtyl, and heteroaryl groups. By using Xing‐Phos as a catalyst, the corresponding products were obtained in good yields, good to high regioselectivity, and excellent diastereo‐ and enantioselectivities (up to 98 % ee ). This methodology allowed the preparation of enantioenriched SF 5 compounds for the first time using an enantioselective approach.