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An Efficient One‐Pot Approach to Bridged Bicyclic Ring‐Systems through Consecutive Hetero‐Domino Transformations: A Mechanistic Rationale and Further Rearrangements
Author(s) -
Finet Laure,
Candela Lena José I.,
Kaoudi Talbi,
Birlirakis Nicolas,
Arseniyadis Siméon
Publication year - 2003
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.200304838
Subject(s) - domino , bicyclic molecule , ring (chemistry) , reagent , olefin fiber , chemistry , lactone , stereochemistry , cascade reaction , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis
This article describes the design of olefin‐generated/reagent‐modulated consecutive hetero‐domino reactions of 1,2‐unsaturated bicyclic diols, which are potentially of great use, initiated by PhI(OAc) 2 , continued by [Pb(OAc) 4 ], and completed by use of a mild base (K 2 CO 3 ). Inversion of a quaternary center has been achieved through a three‐reaction sequence: a domino transformation followed by an m ‐CPBA‐mediated Baeyer–Villiger oxidation and subsequent reductive lactone ring opening.