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From Enantiopure Hydroxyaldehydes to Complex Heterocyclic Scaffolds: Development of Domino Petasis/Diels–Alder and Cross‐Metathesis/Michael Addition Reactions
Author(s) -
Cannillo Alexandre,
Norsikian Stéphanie,
Tran Huu Dau MarieElise,
Retailleau Pascal,
Iorga Bogdan I.,
Beau JeanMarie
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.201402965
Subject(s) - enantiopure drug , domino , michael reaction , salt metathesis reaction , chemistry , combinatorial chemistry , metathesis , selectivity , organic chemistry , catalysis , enantioselective synthesis , polymer , polymerization
One‐step assembly of hexahydroisoindole scaffolds by a sequence that combines the Petasis (borono‐Mannich) and Diels–Alder reactions is described. The unique selectivity observed experimentally was confirmed by quantum calculations. The current method is applicable to a broad range of substrates, including free sugars, and holds significant potential to efficiently and stereoselectively build new heterocyclic structures. This easy and fast entry to functionalized polycyclic compounds can be pursued by further transformations, for example, additional ring closure by a cross‐metathesis/Michael addition domino sequence.