Premium
Sequential Norrish Type II Photoelimination and Intramolecular Aldol Cyclization of 1,2‐Diketones in Carbohydrate Systems: Stereoselective Synthesis of Cyclopentitols
Author(s) -
ÁlvarezDorta Dimitri,
León Elisa I.,
Kennedy Alan R.,
RiescoFagundo Concepción,
Suárez Ernesto
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200803696
Subject(s) - stereoselectivity , pyranose , chemistry , intramolecular force , stereochemistry , aldol reaction , photostimulation , derivative (finance) , isomerization , organic chemistry , catalysis , biochemistry , financial economics , economics
Opened and closed : Visible‐light photostimulation of 2,3‐diuloses I triggers an unprecedented sequential rearrangement: A Norrish type II photoelimination to give an isolable acyclic photoenol intermediate II is followed by an intramolecular enolexo aldolization. The contraction of the pyranose ring in this process leads to a new type of cyclopentitol derivative III . R=acyl, alkyl, silyl group.