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Asymmetric Synthesis of α‐Difluorinated β‐Amino Sulfones through Detrifluoroacetylative Mannich Reactions
Author(s) -
Li Ziyi,
Wang Nana,
Mei Haibo,
Konno Hiroyuki,
Soloshonok Vadim A.,
Han Jianlin
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100350
Subject(s) - chemistry , mannich reaction , yield (engineering) , sulfone , organic chemistry , combinatorial chemistry , reaction conditions , catalysis , materials science , metallurgy
Asymmetric detrifluoroacetylative Mannich reactions between α‐fluorinated arylsulfonyl gem ‐diols and fluoroalkyl imines have been developed under operationally convenient conditions. Varieties of α‐fluorinated arylsulfonyl gem ‐diols and fluoroalkyl imines are well tolerated with the corresponding α‐difluorinated β‐amino sulfone products generated in moderate to excellent yields as well as high diastereoselectivity. The reaction can be reproduced on gram‐scale with uncompromised yield and stereochemical outcome. The synthetic value of the products is demonstrated by two transformations by means of desulfonylation and removal of the sulfinyl protecting‐group.