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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 23
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Original Articles

Deracemization and Transacetalization of Aldehydes with Enantiomers of Betti's Base Derivatives

, , &
Pages 3450-3455 | Received 04 Jun 2014, Published online: 10 Oct 2014
 

Abstract

Improved procedure for the deracemization of α-methyl dihydrocinnamic aldehydes (2-methyl-3-phenylpropanals) with L-(+)-tartaric acid salt of (S)-enantiomer of Betti's base, is presented. The method enabled the transacetalization of N,O-ketal (R)-enantiomer of Betti's base with various aldehydes.

GRAPHICAL ABSTRACT

Notes

a Determined by HPLC on chiral stationary phase, AD-H, hexane/i-PrOH = 9:1, 1 mL/min, 254 nm, 25°C.

a HPLC, AD-H, hexane/i-PrOH = 9:1, 1 mL/min, 254 nm, 20°C. (N,O-ketal of R-enantiomer tR = 3.9). (AD-H, hexane/i-PrOH = 9:1, 1 mL/min, 254 nm, 20°C).

b Based on 1H NMR.

Note. n.a., not applicable.

Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.

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