TY - JOUR
T1 - Propylene glycol cyclic sulfate as a substitute for propylene oxide in reactions with acetylides
AU - Bates, Roderick W.
AU - Maiti, Tushar B.
PY - 2003
Y1 - 2003
N2 - Lithium acetylides react cleanly with propylene glycol cyclic sulfate to give, after acidic hydrolysis, homopropargylic alcohols in good yield. The benzyl and TBDPS protecting groups are stable to these conditions, but the THP, TBS, acetal and orthoester groups are not. The readily available (S)-cyclic sulfate gives the (S)-alcohol without loss of stereochemical integrity.
AB - Lithium acetylides react cleanly with propylene glycol cyclic sulfate to give, after acidic hydrolysis, homopropargylic alcohols in good yield. The benzyl and TBDPS protecting groups are stable to these conditions, but the THP, TBS, acetal and orthoester groups are not. The readily available (S)-cyclic sulfate gives the (S)-alcohol without loss of stereochemical integrity.
UR - http://www.scopus.com/inward/record.url?scp=0037231863&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037231863&partnerID=8YFLogxK
U2 - 10.1081/SCC-120015819
DO - 10.1081/SCC-120015819
M3 - Article
AN - SCOPUS:0037231863
SN - 0039-7911
VL - 33
SP - 633
EP - 640
JO - Synthetic Communications
JF - Synthetic Communications
IS - 4
ER -