Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation

Tao，Lin1; Zhao，Qingyang2,3; Zhang，Xumu1,2; Dong，Xiu Qin1

2020

10.1016/j.cclet.2020.01.001

CHINESE CHEMICAL LETTERS   影响因子和分区

1001-8417

1878-5964

Rh/ZhaoPhos-catalyzed asymmetric hydrogenation of a series of (E)-2-(chroman-4-ylidene)acetates was successfully developed to prepare various chiral 4-substituted chromanes with high yields and excellent enantioselectivities (up to 99% yield, 98% ee). Moreover, the gram-scale hydrogenation could be performed well in the presence of 0.02 mol% catalyst loading (TON = 5 000), the hydrogenation product was easily converted to access other important compounds, which demonstrated the synthetic utility of this asymmetric catalytic methodology.

Asymmetric hydrogenation Bisphosphine-thiourea ligand Chiral 4-substituted chromanes Excellent enantioselectivity Gram-scale synthesis

SCI ; CCR

英语

通讯

National Natural Science Foundation of China[21432007][21502145][21602172] ; Wuhan Morning Light Plan of Youth Science and Technology[2017050304010307] ; Fundamental Research Funds for and the Central Universities[2042018kf0202] ; Shenzhen Nobel Prize Scientists Laboratory Project[C17783101] ; Science and Technology Innovation Committee of Shenzhen[KQTD 20150717103157174]

Chemistry

Chemistry, Multidisciplinary

WOS:000548928800027

ELSEVIER SCIENCE INC

CHEMISTRY

2-s2.0-85077690830

Scopus

1.Key Laboratory of Biomedical Polymers,Engineering Research Centre of Organosilicon Compounds & Materials,Ministry of Education,College of Chemistry and Molecular Sciences,Wuhan University,Wuhan,430072,China
2.Department of Chemistry and Shenzhen Grubbs Institute,Southern University of Science and Technology,Shenzhen,518055,China
3.School of Pharmaceutical Sciences (Shenzhen),Sun Yatsen University,Shenzhen,518107,China

Tao，Lin,Zhao，Qingyang,Zhang，Xumu,et al. Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation[J]. CHINESE CHEMICAL LETTERS,2020,31(7):1859-1862.

Tao，Lin,Zhao，Qingyang,Zhang，Xumu,&Dong，Xiu Qin.(2020).Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation.CHINESE CHEMICAL LETTERS,31(7),1859-1862.

Tao，Lin,et al."Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation".CHINESE CHEMICAL LETTERS 31.7(2020):1859-1862.