Catalyst‐Directed Diastereo‐ and Site‐Selectivity in Successive Nucleophilic and Electrophilic Allylations of Chiral 1,3‐Diols: Protecting‐Group‐Free Synthesis of Substituted Pyrans

Publisher: John Wiley & Sons Inc

E-ISSN: 1521-3765|20|41|13382-13389

ISSN: 0947-6539

Source: CHEMISTRY - A EUROPEAN JOURNAL, Vol.20, Iss.41, 2014-10, pp. : 13382-13389

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Abstract

AbstractThe 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.