Journal of Organic Chemistry p. 2570 - 2576 (1994)
Update date:2022-08-03
Topics:
Ko, Soo Y.
Malik, Majbeen
Dickinson, A. Frances
A method has been developed to access erythro-2,3-diols via Sharpless's asymmetric dihydroxylation reaction.Thus, a TBDMS-protected (E)-allylic alcohol is dihydroxylated and the resulting threo-2,3-diol is converted to the cyclic sulfate.Upon desilylation, this compound undergoes a Payne-type rearrangement.Nucleophilic epoxide-opening then provides an erythro-2,3-diol.The conversions from the cyclic sulfate to the diol product are performed in a single reaction vessel.Due to the irreversible nature of the Payne-type rearrangement, this process is easy to perform and completely regioselective independent of the substrate structures.Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, -N3, -OAc, -CN, halides as well as carbon nucleophiles and hydride.
View Morewebsite:http://www.orchid-chem.com
Contact:+86-571-85395792
Address:607, North Zhongshan Road, Hangzhou 310000 China
Contact:+86-021-6989-5597
Address:No.80 Yichuan Rd., Putuo District,Shanghai,P.R.China
Suzhou Kangrun Pharmaceutical, Inc
Contact:86-512-63912376,63913329
Address:Building 2, No. 2358 ,Chang'an Rd, Wujiang Economic Development Zone Pioneering park, china
website:http://www.sdowchem.com
Contact:86-135-2193 7483
Address:8-106 taiyue building
Zhejiang kehong chemical co., ltd
Contact:0086-575-85522000
Address:xiner center RD binhai industrial zone shaoxing zhejiang province P.R.China,312073
Doi:10.1016/S0040-4039(00)98734-3
(1985)Doi:10.1007/s10593-007-0045-6
(2007)Doi:10.1021/jf101064v
(2010)Doi:10.1021/jo800382p
(2008)Doi:10.1248/cpb.35.2228
(1987)Doi:10.1002/jlcr.1242
(2007)