TY - JOUR
T1 - Catalytic asymmetric epoxidation of α-methyl α,β- unsaturated anilides as ester surrogates
AU - Chen, Zhihua
AU - Morimoto, Hiroyuki
AU - Matsunaga, Shigeki
AU - Shibasaki, Masakatsu
PY - 2006/12/18
Y1 - 2006/12/18
N2 - Catalytic asymmetric epoxidation of α-methyl α,β- unsaturated carboxylic acid derivatives was achieved using anilide as a template. The Pr(Oi-Pr)3-6,6́-Ph-BINOL complex (10 mol%) with a Ph3P(O) (30 mol%) additive promoted the epoxidation of anilides in up to 99% yield and 88% ee. For α-methyl-β-Ph α,β- unsaturated anilide, the Gd(Oi-Pr)3-6,6′-I-BINOL complex (10 mol%) with Ar3P(O) (30 mol%, Ar = 4-methoxyphenyl) was suitable, giving epoxide in 87% yield and 78% ee.
AB - Catalytic asymmetric epoxidation of α-methyl α,β- unsaturated carboxylic acid derivatives was achieved using anilide as a template. The Pr(Oi-Pr)3-6,6́-Ph-BINOL complex (10 mol%) with a Ph3P(O) (30 mol%) additive promoted the epoxidation of anilides in up to 99% yield and 88% ee. For α-methyl-β-Ph α,β- unsaturated anilide, the Gd(Oi-Pr)3-6,6′-I-BINOL complex (10 mol%) with Ar3P(O) (30 mol%, Ar = 4-methoxyphenyl) was suitable, giving epoxide in 87% yield and 78% ee.
UR - http://www.scopus.com/inward/record.url?scp=33846473111&partnerID=8YFLogxK
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U2 - 10.1055/s-2006-956491
DO - 10.1055/s-2006-956491
M3 - Article
AN - SCOPUS:33846473111
SN - 0936-5214
SP - 3529
EP - 3532
JO - Synlett
JF - Synlett
IS - 20
ER -