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. 2018 Sep 28;8(58):33451-33458.
doi: 10.1039/c8ra06615a. eCollection 2018 Sep 24.

Asymmetric vinylogous aldol addition of alkylidene oxindoles on trifluoromethyl-α,β-unsaturated ketones

Simone Crotti  1 , Giada Belletti  1 , Nicola Di Iorio  1 , Emanuela Marotta  1 , Andrea Mazzanti  1 , Paolo Righi  1 , Giorgio Bencivenni  1
Affiliations

Asymmetric vinylogous aldol addition of alkylidene oxindoles on trifluoromethyl-α,β-unsaturated ketones

Simone Crotti et al. RSC Adv. .

Abstract

A novel vinylogous aldol addition of alkylidene oxindole with 1-trifluoromethyl-3-alkylidene-propan-2-ones is presented. The reaction, catalyzed by a bifunctional tertiary amine, provides an efficient application of the vinylogous reactivity of oxindoles for the preparation of enantioenriched trifluoromethylated allylic alcohols.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. (a) Biologically active alkylidene oxindole. (b) Typical reactivity of alkylidene oxindoles.
Fig. 2
Fig. 2. Biologically active trifluoromethyl compounds.
Scheme 1
Scheme 1. Strategic plan for the vinylogous aldol addition.
Fig. 3
Fig. 3. Important biologically active allylic alcohols.
Scheme 2
Scheme 2. Synthesis and X-ray structure of compound 5aa.
Fig. 4
Fig. 4. Proposed transition state models derived from DFT calculations. Modes A-(Si)-s-cis and B-(Si)-s-cis contributes to the formation of the major (R)-3aa as observed. The minor enantiomer (S)-3aa is the results of the mode B-(Re)-s-cis way of action of the catalyst V.
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