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Synthesis of Stannyl‐Substituted d ‐Glucal Derivatives via Palladium‐Catalyzed Regioselective Hydrostannation and Their Synthetic Applications
Author(s) -
Shamim Anwar,
Barbeiro Criatiane S.,
Ali Bakhat,
Stefani Hélio A.
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601232
Subject(s) - regioselectivity , glucal , chemistry , sonogashira coupling , substituent , palladium , alkyne , stille reaction , catalysis , stereochemistry , organic chemistry , medicinal chemistry
Stannyl derivatives of 2‐alkenyl acetylated D‐glucals have been synthesized via palladium‐catalyzed regioselective hydrostannation in good yields under mild reaction conditions. Factors affecting the regioselectivity of hydrostannation including chelation by the neighbouring acetyl‐oxygen and the electronic effect of the substituent R on alkyne have been evaluated. The synthetic applications of these stannyl derivatives of D‐glucal are shown by performing Stille and Sonogashira cross‐coupling reactions to obtain a library of substituted 2‐alkenyl derivatives of D‐glucal.