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

Add time:08/26/2019    Source:sciencedirect.com

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.

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