A sequential indium-mediated aldehyde allylation/palladium-catalyzed cross-coupling reaction in the synthesis of 2-deoxy-beta-C-aryl glycosides.
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.
Moral
John Alec
JA
Department of Chemistry and Biochemistry, California State University-Northridge, Northridge, California 91330, USA.
Moon
Seong-Jin
SJ
Rodriguez-Torres
Samuel
S
Minehan
Thomas G
TG
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D007204:Indium / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D006027:Glycosides; D007204:Indium; D010165:Palladium