Total diastereoselectivity in the one-pot multistep reaction of ( R S)-(+)-{[(4-methylphenyl)sulfinyl]methyl}-1-oxa-4-azaspiro[4.5]dec-3-ene and E-methyl cinnamate. An approach to (2 S,4 S,5 R,6 R)-2-(hydroxymethyl)-4,6-diphenyl-1-azabicycle[3.3.1]nonane

The base-mediated reaction of enantiomerically pure α-sulfinylketimine (+)- 1 with ( E)-methyl cinnamate afforded (+)- 5a in a one-pot procedure with complete diastereoselectivity. A sole diastereomer of the eight possible ones was isolated which revealed the stereocontrol of the chiral sulfinyl gro...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2008-06, Vol.19 (12), p.1411-1413
Main Authors: Alvarez-Ibarra, Carlos, Collados Luján, Juan F., Quiroga-Feijóo, Maria L., Rodríguez, Gonzalo
Format: Article
Language:English
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Summary:The base-mediated reaction of enantiomerically pure α-sulfinylketimine (+)- 1 with ( E)-methyl cinnamate afforded (+)- 5a in a one-pot procedure with complete diastereoselectivity. A sole diastereomer of the eight possible ones was isolated which revealed the stereocontrol of the chiral sulfinyl group in the construction of the three new stereogenic centres. The absolute configuration of stereocentres introduced in (+)- 5a was assigned on the basis of 1H NMR data and a single X-ray structure.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2008.05.030