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. 2019 May 17;9(27):15466-15469.
doi: 10.1039/c9ra02694k. eCollection 2019 May 14.

Efficient access to chiral dihydrobenzoxazinones via Rh-catalyzed hydrogenation

Ziyi Chen  1 , Xuguang Yin  1 , Xiu-Qin Dong  1 , Xumu Zhang  1   2
Affiliations

Efficient access to chiral dihydrobenzoxazinones via Rh-catalyzed hydrogenation

Ziyi Chen et al. RSC Adv. .

Abstract

Rh/(S)-DTBM-SegPhos-catalyzed asymmetric hydrogenation of prochiral (Z)-2-(2-oxo-2H-benzo[b][1,4]oxazin-3(4H)-ylidene)acetate esters was successfully developed. A series of chiral dihydrobenzoxazinones were prepared through this efficient methodology with good to excellent results (up to >99% conversion, 93% yield and >99% ee), which are important motifs in the biologically active molecules.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Fig. 1
Fig. 1. Examples of biologically active molecules containing chiral dihydrobenzoxazinone or related framework.
Scheme 1
Scheme 1. Preparation of chiral dihydrobenzoxazinones through Rh-catalyzed asymmetric hydrogenation.
Fig. 2
Fig. 2. The structure of chiral diphosphine ligands.
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