Bulletin of the Chemical Society of Japan p. 2917 - 2921 (1982)
Update date:2022-08-02
Topics:
Yamashita, Mitsuji
Hiramatsu, Koji
Yamada, Manabu
Suzuki, Nobuyoshi
Inokawa, Saburo
Diphenylphosphine and diphenylphosphinite derivatives of sugars such as methyl 6-deoxy-4-C-(diphenylphosphino)-2,3-O-isopropylidene-α-L-talopyranoside, methyl 4-O-(diphenylphosphino)-2,3-O-isopropylidene-α-L-rhamnopyranoside, methyl 4-C,4-O-(diphenylphosphino)-2,3-O-isopropylidene-α-L-talopyranoside, 6-deoxy-6-C-(diphenylphosphino)-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose, and 6-O-(diphenylphosphino)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose were synthesized by the reaction of diphenylphosphine-sodium dihydrobis(2-methoxyethoxy)aluminate (SDMA) and/or diphenylphosphinous chloride-triethylamine with sugar derivatives.Homogeneous asymmetric hydrogenations of several prochiral olefins (α-acetylaminocinnamic acid, methyl α-acetylaminocinnamate, α-benzoylaminocinnamic acid, itaconic acid, and tiglic acid) were carried out using rhodium(I) catalysts with the tervalent chiral phosphorus derivatives of sugars.The highest optical yield for all the five substrates was obtained when di-μ-chloro-bis(cyclooctadiene)dirhodium(I) and 6-O-(diphenylphosphino)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose were used.The advantages of this method are the simplicity in the synthesis of the chiral phosphorus compound and the comparatively high optical yield in the asymmetric hydrogenation of olefins.
View MoreChengdu Baishixing Science and Technology Industry Co., Ltd.
website:http://www.cd-bsx.com
Contact:+86-28-88531548
Address:#217,North of Industry Road,Heshan Town,Pujiang County,Chengdu,Sichuan,China.
JIANGXI XINXIN CHEMICAL CO., LTD.
Contact:86-15957176628
Address:INDUSTRY ROAD 1, INDUSTRIAL PARK, HEKOU TOWN,YANSHAN COUNTY, JIANGXI PROVINCE, CHINA
Shanghai Pinewood Fine Chemical Co., Ltd.
website:http://www.pinewoodchem.com
Contact:0086-21-62417129,62414096
Address:Suite B, 27F, No.2, Lane 600, Tianshan Road, Shanghai
Jiangxi Global Natural Spice Co., Ltd.
Contact:+86-796-8106598
Address:No.89, Wenshan Road,South Industrial Park, Jishui County,Jiangxi Province
Jinhua City Mingzhu Pharmaceutical Co.,Ltd.
Contact:15857995878 0579-82207761
Address:No.169 Shenze Road, New Area,Jinpan Development Zone, Jinhua
Doi:10.1021/jo00152a029
(1983)Doi:10.1246/bcsj.55.3657
(1982)Doi:10.1021/jo00153a016
(1983)Doi:10.1016/S0031-9422(82)85056-5
(1982)Doi:10.1016/S0040-4039(00)87707-2
(1982)Doi:10.1021/acs.orglett.5b03664
(2016)