TY - JOUR
T1 - Guanidine bases in synthesis
T2 - Extending the scope of the corey-chaykovsky epoxidation
AU - Phillips, David J.
AU - Graham, Andrew E.
PY - 2010
Y1 - 2010
N2 - Guanidine bases, such as 1,5,7-triazabicyclo[4.4.0]dec-1-ene (TBD) or 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-1-ene (MTBD), are highly effective reagents for the in situ generation of sulfonium ylides from sulfonium salts in Corey-Chaykovsky epoxidation reactions of aldehydes. These reactions proceed rapidly to produce the corresponding epoxides in excellent yields and with high selectivity for the trans product. Significantly, this reagent combination is applicable to both nonenolizable and enolizable aldehydes and α,β-unsaturated aldehydes.
AB - Guanidine bases, such as 1,5,7-triazabicyclo[4.4.0]dec-1-ene (TBD) or 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-1-ene (MTBD), are highly effective reagents for the in situ generation of sulfonium ylides from sulfonium salts in Corey-Chaykovsky epoxidation reactions of aldehydes. These reactions proceed rapidly to produce the corresponding epoxides in excellent yields and with high selectivity for the trans product. Significantly, this reagent combination is applicable to both nonenolizable and enolizable aldehydes and α,β-unsaturated aldehydes.
KW - Corey-Chaykovsky epoxidation
KW - Enolizable aldehydes
KW - Epoxides
KW - Guanidine bases
KW - In situ ylide generation
U2 - 10.1055/s-0029-1219359
DO - 10.1055/s-0029-1219359
M3 - Article
AN - SCOPUS:77749283853
SP - 769
EP - 773
JO - Synlett
JF - Synlett
SN - 0936-5214
IS - 5
M1 - D30409ST
ER -