Sequential Norrish Type II Photoelimination and Intramolecular Aldol Cyclization of 1,2‐Diketones in Carbohydrate Systems: Stereoselective Synthesis of Cyclopentitols | Zendy

ÁlvarezDorta Dimitri | Zendy; León Elisa I. | Zendy; Kennedy Alan R. | Zendy; RiescoFagundo Concepción | Zendy; Suárez Ernesto | Zendy

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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.

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