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Diversity‐Oriented Synthesis of Enantiopure Furofurans from Carbohydrates: An Expedient Approach with Built‐in Michael Acceptor, Masked Aldehyde and Leaving Group in a Single Sugar Derivative
Author(s) -
Manna Chinmoy,
Pathak Tanmaya
Publication year - 2013
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.201300603
Subject(s) - chemistry , stereocenter , enantiopure drug , aldehyde , michael reaction , reagent , stereochemistry , asymmetric induction , acceptor , bicyclic molecule , derivative (finance) , leaving group , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , physics , financial economics , economics , condensed matter physics
Abstract A single sugar molecule containing three functional groups, namely a masked aldehyde, a Michael acceptor and a leaving group, reacts with a series of β‐dicarbonyl compounds and related reagents to form up to three new bonds and up to three new stereocenters. The configuration of the sugar derivative controls the diastereoselectivity in the formation of all the new bonds without a requirement for any external reagent for asymmetric induction. This “Chiral pool” based diversity‐oriented synthetic strategy has led to the formation of a series of furofurans based on different scaffolds and with appendage variations, and also to a hitherto unknown family of bicyclic 3,8‐dioxabicyclo[4.2.1]nonanes.