An Efficient One‐Pot Approach to Bridged Bicyclic Ring‐Systems through Consecutive Hetero‐Domino Transformations: A Mechanistic Rationale and Further Rearrangements | Zendy

Finet Laure | Zendy; Candela Lena José I. | Zendy; Kaoudi Talbi | Zendy; Birlirakis Nicolas | Zendy; Arseniyadis Siméon | Zendy

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research