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The aldol reaction between the aluminium enolate derived from (S)-[(η<sup>5</sup>-C<inf>5</inf>H<inf>5</inf>)Fe(CO)(PPh<inf>3</inf>)(Ac)] (S)-(3) and Boc-L-prolinal (S)-(2) gives, after deprotection and decomplexation, (1R,8S)-1-hydroxypyrrolizidin-3-one, (1), while its epimer (1S,8S)-(1) is obtained in a similar way from (R)-(3), the inherent stereocontrol of (2) being overpowered by the iron chiral auxiliary.

Original publication

DOI

10.1039/C39880000160

Type

Journal article

Journal

Journal of the Chemical Society, Chemical Communications

Publication Date

01/01/1988

Pages

160 - 161