TY - JOUR
T1 - An Access to erythro-Diola via Sharpless's Asymmetric Dihydroxylation Reaction
AU - Ko, Soo Y.
AU - Malik, Majbeen
AU - Dickinson, A. Frances
PY - 1994/5/1
Y1 - 1994/5/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0001400685&partnerID=8YFLogxK
U2 - 10.1021/jo00088a045
DO - 10.1021/jo00088a045
M3 - Article
AN - SCOPUS:0001400685
SN - 0022-3263
VL - 59
SP - 2570
EP - 2576
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 9
ER -