Efficient synthesis of chiral 2,3-dihydro-benzo[b]thiophene 1,1-dioxides via Rh-catalyzed hydrogenation† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c8sc05397a

Content Provider	Semantic Scholar
Author	Liu, Gongyi Zhang, Heng Huang, Yi Han, Zhengyu Liu, Gang Liu, Yuanhua Dong, Xiu-Qin Zhang, Xumu
Copyright Year	2019
Abstract	Rh-catalyzed asymmetric hydrogenation of prochiral substituted benzo[b]thiophene 1,1-dioxides was successfully developed, affording various chiral 2,3-dihydrobenzo[b]thiophene 1,1-dioxides with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). In particular, for challenging substrates, such as aryl substituted substrates with sterically hindered groups and alkyl substituted substrates, the reaction proceeded smoothly in our catalytic system with excellent results. The gram-scale asymmetric hydrogenation proceeded well with 99% yield and 99% ee in the presence of 0.02 mol% (S/C = 5000) catalyst loading. The possible hydrogen-bonding interaction between the substrate and the ligand may play an important role in achieving high reactivity and excellent enantioselectivity.
Starting Page	2507
Ending Page	2512
Page Count	6
File Format	PDF HTM / HTML
DOI	10.1039/c8sc05397a
Alternate Webpage(s)	https://pubs.rsc.org/en/content/articlepdf/2019/sc/c8sc05397a
Alternate Webpage(s)	http://www.rsc.org/suppdata/c8/sc/c8sc05397a/c8sc05397a1.pdf
PubMed reference number	30881681
Alternate Webpage(s)	https://doi.org/10.1039/c8sc05397a
Journal	Medline
Volume Number	10
Journal	Chemical science
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article