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Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides.

ABSTRACT: 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.

SUBMITTER: Marcyk PT

PROVIDER: S-EPMC6489501 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides.

Marcyk Paul T PT Jefferies Latisha R LR AbuSalim Deyaa I DI Pink Maren M Baik Mu-Hyun MH Cook Silas P SP

Angewandte Chemie (International ed. in English) 20190115 6

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 p ...[more]

PMID: 30536739

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