Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst

Takatsugu Murata; Tatsuya Kawanishi; Akihiro Sekiguchi; Keisuke Ono; Kenya Nakata; Isamu Shiina

doi:10.20944/preprints201807.0414.v1

A peer-reviewed article of this Preprint also exists.

Murata, T.; Kawanishi, T.; Sekiguchi, A.; Ishikawa, R.; Ono, K.; Nakata, K.; Shiina, I. Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst. Molecules 2018, 23, 2003. Murata, T.; Kawanishi, T.; Sekiguchi, A.; Ishikawa, R.; Ono, K.; Nakata, K.; Shiina, I. Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst. Molecules 2018, 23, 2003.

Abstract

Various optically active 2-hydroxyamide derivatives are produced based on the kinetic resolution of racemic 2-hydroxyamides with a diphenylacetyl component and (R)-benzotetramisole [(R)-BTM], a chiral acyl-transfer catalyst, via asymmetric esterification and acylation. It was revealed that a tertiary amide can be used with this novel protocol to achieve high selectivity [22 examples; s-value reaching over 250]. The resulting chiral compounds could be transformed into other useful structures while maintaining their chirality.

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Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst

Abstract

Keywords

Subject

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