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. 2008 Nov 6;10(21):4811-4.
doi: 10.1021/ol801971t. Epub 2008 Oct 3.

L-selectride-mediated highly diastereoselective asymmetric reductive aldol reaction: access to an important subunit for bioactive molecules

Arun K Ghosh  1 , Jorden Kass, David D Anderson, Xiaoming Xu, Christine Marian
Affiliations

L-selectride-mediated highly diastereoselective asymmetric reductive aldol reaction: access to an important subunit for bioactive molecules

Arun K Ghosh et al. Org Lett. .

Abstract

L-selectride reduction of a chiral or achiral enone followed by reaction of the resulting enolate with optically active alpha-alkoxy aldehydes proceeded with excellent diastereoselectivity. The resulting alpha,alpha-dimethyl-beta-hydroxy ketones are inherent to a variety of biologically active natural products.

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Figures

Figure 1
Figure 1
Reductive aldol reaction of 1 and 2
Scheme 1
Scheme 1
Asymmetric reductive aldol reaction with chiral enone and chiral aldehydes
Figure 2
Figure 2
Stereochemical model for aldol reactions
Scheme 2
Scheme 2
Synthesis of enones 10, 12 and 13
Scheme 3
Scheme 3
Synthesis of 9 and aldol reaction of 14
See this image and copyright information in PMC

References

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