Methods for the preparation of 1,3-amino alcohols and their derivatives containing two stereogenic centers usually involve a two-step installation of the chiral centers. An aldol-Tishchenko reaction of chiral sulfinimines which involves the first reported reduction of a C═N in this type of reaction is described. Two and even three chiral centers can be installed in one synthetic step, affording anti-1,3-amino alcohols in good diastereo- and enantioselectivity.

Procedures yielding ( S )‐2‐Methyl‐ N ‐(1‐phenylethylidene)propane‐2‐sulfinamide 3 as two fractions of a yellow solid and (1 S ,3 S )‐1‐((( S )‐ tert ‐butylsulfinyl)amino)‐4‐methyl‐1‐phenylpentan‐3‐yl isobutyrate as a pale yellow oil are presented. A discussion on 1,3‐aminoalcohols as useful synthetic intermediates and building blocks concludes the chapter.

The asymmetric alkylation of ketones represents a fundamental transformation in organic chemistry. Chiral auxiliaries have been used almost exclusively for this transformation. Herein we describe a strategy for the generation of enantiomerically enriched α-alkylated ketones up to an er of 83 : 17, using a chiral ligand protocol.

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The first example of an aldol—Tishchenko reduction of imines is reported.