A Mild, Diastereoselective Construction of Cyclic and Spirocyclic Ketals Employing a Tandem Photoisomerization/Cyclization Tactic | Zendy

Bo Li | Zendy; Brett Williams | Zendy; Amos B. Smith | Zendy

Open Access

A Mild, Diastereoselective Construction of Cyclic and Spirocyclic Ketals Employing a Tandem Photoisomerization/Cyclization Tactic

Author(s) -

Bo Li,

Brett Williams,

Amos B. Smith

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol503116q

Subject(s) - photoisomerization , chemistry , tandem , catalysis , combinatorial chemistry , surface modification , organic chemistry , isomerization , materials science , composite material

The cyclization of trans-δ-hydroxy enones to cyclic mixed ketals routinely requires superstoichiometric strong acid. By operating under a photoisomerization regime, the cyclization of trans-δ-hydroxy enones proceeds under catalytic Brønsted acid to provide cyclic ketals or unsaturated spiroketals in a highly diastereoselective fashion. A one-pot, two-step protocol was thus developed to provide cyclic methoxy ketals with a free β-hydroxy group for future functionalization.

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