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Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible‐Light‐Mediated Deoxygenation
Author(s) -
Rackl Daniel,
Kais Viktor,
Lutsker Eugen,
Reiser and Oliver
Publication year - 2017
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.201700014
Subject(s) - deoxygenation , chemistry , visible spectrum , radical , benzoates , trifluoromethyl , alkyl , irradiation , organic chemistry , photochemistry , combinatorial chemistry , catalysis , physics , optoelectronics , nuclear physics
The synthesis of chiral tetrahydrofurans and pyrrolidines starting from 1,2‐diols or β‐amino alcohols, respectively, by visible‐light‐mediated deoxygenation is described. Easily accessible monoallylated/propargylated substrates were activated either as inexpensive ethyl oxalates or as recyclable 3,5‐bis(trifluoromethyl)benzoates to generate alkyl radicals suitable for 5‐ exo ‐ trig /5‐ exo ‐ dig cyclizations under visible‐light irradiation.