Efficient access to chiral dihydrobenzoxazinones <i>via</i> Rh-catalyzed hydrogenation

Chen, Ziyi; Yin, Xuguang; Dong, Xiu‐Qin; Zhang, Xumu

doi:10.1039/c9ra02694k

Search citation statements

Order By: Relevance

Paper Sections

Select...

αβ-Unsaturated Lactones1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2020

2024

Publication Types

Select...

Article2

Relationship

Self Cite0

Independent2

Authors

Journals

Cited by 2 publications

(1 citation statement)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Chiral dihydrobenzoxazinones P34 were synthesized by a stereoselective Rh/DTBM-SegPhos L40 catalyzed hydrogenation. Dong 76 reported the smooth preparation of these motifs under 20 bar hydrogen atmosphere in up to >99% ee (Scheme 26). The thiourea bisphosphine based ligand ZhaoPhos L8 was proven successful in the rhodium catalyzed asymmetric hydrogenation of maleic anhydrides 77 S35 (up to 99% ee, Dong & Zhang, Scheme 27).…”

Section: αβ-Unsaturated Lactonesmentioning

confidence: 99%

Recent advances in the metal-catalyzed asymmetric alkene hydrogenation of cyclic conjugated carbonyl compounds

Tan,

Peters,

Andersson

et al. 2024

Org. Chem. Front.

View full text Add to dashboard Cite

show abstract

Section: αβ-Unsaturated Lactonesmentioning

confidence: 99%

Recent advances in the metal-catalyzed asymmetric alkene hydrogenation of cyclic conjugated carbonyl compounds

Tan,

Peters,

Andersson

et al. 2024

Org. Chem. Front.

View full text Add to dashboard Cite

show abstract

Selective Construction of Diverse Polycyclic Spirooxindoles via a Three-Component Reaction of Cyclic Mercapto-Substituted β-Enamino Esters, Isatins, and Cyclic 1,3-Diketones

Sun

Pan

et al. 2020

J. Org. Chem.

View full text Add to dashboard Cite

The three-component reaction of alkyl 2-(benzo[b][1,4]thiazin-3-ylidene)acetates, isatins, and 1,3-indanedione (1,3cyclopentanedione) in ethanol in the presence of acetic acid conveniently afforded spiro[indeno[1,2-b]phenothiazine-6,3′-indolines] or spiro[cyclopenta[b]phenothiazine-4,3′-indolines] in good yields and with high diastereoselectivity. More interestingly, a similar three-component reaction with 4-hydroxychromen-2-one resulted in the unexpected polycyclic spiro[benzo[b]chromeno[3′,4′:5,6]pyrano[2,3-e][1,4]thiazine-7,3′-indolines] in satisfactory yields. A plausible reaction mechanism was rationally proposed for formation of different kinds of the spiro compounds, and the stereochemistries of the various spiro compounds were clearly elucidated.

show abstract

Efficient access to chiral dihydrobenzoxazinones via Rh-catalyzed hydrogenation

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 to prepare various chiral dihydrobenzoxazinones with good to excellent results.

Cited by 2 publications

References 36 publications

Recent advances in the metal-catalyzed asymmetric alkene hydrogenation of cyclic conjugated carbonyl compounds

Recent advances in the metal-catalyzed asymmetric alkene hydrogenation of cyclic conjugated carbonyl compounds

Selective Construction of Diverse Polycyclic Spirooxindoles via a Three-Component Reaction of Cyclic Mercapto-Substituted β-Enamino Esters, Isatins, and Cyclic 1,3-Diketones

Contact Info

Product

Resources

About