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. 2009 Aug 20;11(16):3734-7.
doi: 10.1021/ol901353f.

A sequential indium-mediated aldehyde allylation/palladium-catalyzed cross-coupling reaction in the synthesis of 2-deoxy-beta-C-aryl glycosides

John Alec Moral  1 , Seong-Jin Moon, Samuel Rodriguez-Torres, Thomas G Minehan
Affiliations

A sequential indium-mediated aldehyde allylation/palladium-catalyzed cross-coupling reaction in the synthesis of 2-deoxy-beta-C-aryl glycosides

John Alec Moral et al. Org Lett. .

Abstract

Indium-mediated allylation of aldehydes with 2-chloro-3-iodopropene, followed by a palladium-catalyzed cross-coupling reaction with triarylindium reagents or arylboronic acids, leads to aryl-substituted homoallylic alcohols in good to excellent yields and diastereoselectivities. The products obtained from reactions conducted with d-glyceraldehyde acetonide can be transformed into 2-deoxy-beta-C-aryl ribofuranosides in high overall yields. Similarly, 2-deoxy-beta-C-aryl allopyranosides may be prepared efficiently from 2,4-O-benzylidene erythrose.

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Figures

Scheme 1
Scheme 1
Glyceraldehyde allylation with 2,3-dihalopropenes
Scheme 2
Scheme 2
Synthesis of substrates containing sterically-hindered aryl moieties
Scheme 3
Scheme 3
Synthesis of 2-deoxy-C-arylfuranosides 10 from 5
Scheme 4
Scheme 4
Diastereoselective allylation of 2,4-O-benzylidene erythrose 11
Scheme 5
Scheme 5
Synthesis of 2-deoxy β-C-aryl glycosides 15a-c
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