Issue 8, 2013
From the journal:

Chemical Science

Controlling stereochemistry in polyketide synthesis: 1,3- vs. 1,2-asymmetric induction in methyl ketone aldol additions to β-super siloxy aldehydes†

Patrick B. Brady,a   Brian J. Albert,‡a   Matsujiro Akakurab  and  Hisashi Yamamotoac  

a Department of Chemistry, University of Chicago, 5737 S. Ellis Ave, Chicago, IL 60637, USA
E-mail: yamamoto@uchicago.edu
Tel: +1 773 702 5059

b Aichi University of Education, Igaya-cho, Kariya, Aichi 448-8542, Japan

c Molecular Catalyst Research Center, Chubu University, 1200 Matsumoto, Kasugai, Aichi 487-8501, Japan

Abstract

The aldol addition of methyl ketones to β-siloxy and α-methyl β-siloxy aldehydes is described. Careful control of mechanistically distinct aldol reactions leverages 1,2- and 1,3-asymmetric induction, selectively forming syn and anti aldol adducts with excellent diastereocontrol. Experimental and theoretical investigations have provided insight to the factors governing diastereoselectivity.

Graphical abstract: Controlling stereochemistry in polyketide synthesis: 1,3- vs. 1,2-asymmetric induction in methyl ketone aldol additions to β-super siloxy aldehydes

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Article information

DOI
https://doi.org/10.1039/C3SC51183A
Article type
Edge Article
Submitted
30 Apr 2013
Accepted
24 May 2013
First published
28 May 2013

Chem. Sci., 2013,4, 3223-3231

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Controlling stereochemistry in polyketide synthesis: 1,3- vs. 1,2-asymmetric induction in methyl ketone aldol additions to β-super siloxy aldehydes

P. B. Brady, B. J. Albert, M. Akakura and H. Yamamoto, Chem. Sci., 2013, 4, 3223 DOI: 10.1039/C3SC51183A

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