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. 2023 Jan 4;13(2):888-894.
doi: 10.1039/d2ra06272k. eCollection 2023 Jan 3.

New boro amino amide organocatalysts for asymmetric cross aldol reaction of ketones with carbonyl compounds

Zubeda Begum  1 , Chigusa Seki  1 , Yuko Okuyama  2 , Eunsang Kwon  3 , Koji Uwai  1 , Michio Tokiwa  4 , Suguru Tokiwa  4 , Mitsuhiro Takeshita  4 , Hiroto Nakano  1
Affiliations

New boro amino amide organocatalysts for asymmetric cross aldol reaction of ketones with carbonyl compounds

Zubeda Begum et al. RSC Adv. .

Abstract

Distinct types of new boron fused primary amino amide organocatalysts were designed and synthesized from commercially available amino acids. Their catalytic activities were investigated in asymmetric crossed aldol reaction of ketones with aromatic aldehydes to afford the corresponding chiral anti-aldol adducts with good chemical yields, moderate diastereoselectivity and good to excellent enantioselectivities (up to 94% yields, up to 90 : 10 dr, up to 94% ee).

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Asymmetric cross aldol reaction of ketones with carbonyl compounds.
Scheme 2
Scheme 2. Preparations of catalysts 4a–h.
Scheme 3
Scheme 3. Aldol reaction under Whiting et al. condition.
Scheme 4
Scheme 4. The aldol reactions of 5a–h with different aromatic aldehydes 6b–k.
Scheme 5
Scheme 5. Plausible reaction course of the reaction.
Fig. 1
Fig. 1. Scan of total energies (up) and DFT optimized structures (down, at the B3LYP/6-31G(d) level of theory) of the enamine intermediate I generated by varying the torsion angles (the dihedral scans showed with u-shaped arrows: I-1).
Fig. 2
Fig. 2. The scan of total energies for I-A and I-A′.
Fig. 3
Fig. 3. Scan of total energies (up) and DFT optimized structures (down, at the B3LYP/6-31G(d) level of theory) of 6a generated by varying the torsion angles (the dihedral scans showed with u-shaped arrows).
Fig. 4
Fig. 4. The frontier orbital between I-1 and 6a.
See this image and copyright information in PMC

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