Issue 3, 2015

4-Alkenyl-5H-1,2,3-oxathiazole 2,2-dioxides in catalytic and enantioselective [4 + 2] cycloaddition through iminium activation. Straightforward access to the trans-decaline framework and to densely functionalized cyclohexanes

Abstract

We have employed 4-alkenyl-5H-1,2,3-oxathiazole 2,2-dioxides as useful reagents able to generate in situ an electron-rich diene intermediate that has the potential to undergo [4 + 2] cycloaddition with α,β-unsaturated aldehydes through the iminium/enamine activation. Under the optimized reaction conditions that comprise the use of O-TMS diphenylprolinol as an organocatalyst and a Brønsted base as a cocatalyst, a series of [4 + 2] cycloadducts has been prepared as single diastereoisomers with very high enantiomeric excess. Moreover, the cyclic sulfamidate entity can play the role of a masked β-aminoalcohol moiety in which these adducts can be converted by simple diastereoselective reduction/hydrolysis.

Graphical abstract: 4-Alkenyl-5H-1,2,3-oxathiazole 2,2-dioxides in catalytic and enantioselective [4 + 2] cycloaddition through iminium activation. Straightforward access to the trans-decaline framework and to densely functionalized cyclohexanes

Supplementary files

Article information

Article type
Research Article
Submitted
01 Tsh 2014
Accepted
23 Phe 2015
First published
26 Phe 2015

Org. Chem. Front., 2015,2, 206-210

4-Alkenyl-5H-1,2,3-oxathiazole 2,2-dioxides in catalytic and enantioselective [4 + 2] cycloaddition through iminium activation. Straightforward access to the trans-decaline framework and to densely functionalized cyclohexanes

I. Riaño, U. Uria, L. Carrillo, E. Reyes and J. L. Vicario, Org. Chem. Front., 2015, 2, 206 DOI: 10.1039/C4QO00316K

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