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Catalyst‐Directed Diastereo‐ and Site‐Selectivity in Successive Nucleophilic and Electrophilic Allylations of Chiral 1,3‐Diols: Protecting‐Group‐Free Synthesis of Substituted Pyrans
Author(s) -
Shin Inji,
Wang Gang,
Krische Michael J.
Publication year - 2014
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.201404065
Subject(s) - electrophile , nucleophile , chemistry , aldehyde , protecting group , alcohol , catalysis , reagent , iridium , selectivity , enantioselective synthesis , organic chemistry , combinatorial chemistry , alkyl
The iridium‐catalyzed, protecting group‐free synthesis of 4‐hydroxy‐2,6‐ cis ‐ or trans ‐pyrans through successive nucleophilic and electrophilic allylations of chiral 1,3‐diols occurs with complete levels of catalyst‐directed diastereoselectivity in the absence of protecting groups, premetallated reagents, or discrete alcohol‐to‐aldehyde redox reactions.