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Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides
Author(s) -
Marcyk Paul T.,
Jefferies Latisha R.,
AbuSalim Deyaa I.,
Pink Maren,
Baik MuHyun,
Cook Silas P.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201812894
Subject(s) - chemistry , electrophile , intramolecular force , catalysis , hydroamination , alcohol , derivatization , combinatorial chemistry , solvolysis , organic chemistry , hydrolysis , high performance liquid chromatography
The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo‐outcomes presents an even more formidable challenge. Described herein is a simple iron‐based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2‐ and 2,2‐subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.