TY - JOUR
T1 - Lithium n-benzyltrimethylsilylamide (LSA)
T2 - a new reagent for conjugate addition - enolate trapping reactions
AU - Asao, Naoki
AU - Uyehara, Tadao
AU - Yamamoto, Yoshinori
PY - 1988
Y1 - 1988
N2 - Lithium N-benzyltrimethylsilyl amide (LSA) adds to crotonates in a 1,4-manner, though the reaction of ordinary lithium amides with α,β-unsaturated carbonyl compounds is accompanied with a 1,2-addition and hydrogen abstraction at the γ-position. The conjugate addition via LSA followed by enolate trapping with electrophiles produces the corresponding α-substituted β-amino esters, which are, in turn, converted into β-lactams and α-substituted α, β-unsaturated esters.
AB - Lithium N-benzyltrimethylsilyl amide (LSA) adds to crotonates in a 1,4-manner, though the reaction of ordinary lithium amides with α,β-unsaturated carbonyl compounds is accompanied with a 1,2-addition and hydrogen abstraction at the γ-position. The conjugate addition via LSA followed by enolate trapping with electrophiles produces the corresponding α-substituted β-amino esters, which are, in turn, converted into β-lactams and α-substituted α, β-unsaturated esters.
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U2 - 10.1016/S0040-4020(01)86664-3
DO - 10.1016/S0040-4020(01)86664-3
M3 - Article
AN - SCOPUS:0000753162
SN - 0040-4020
VL - 44
SP - 4173
EP - 4180
JO - Tetrahedron
JF - Tetrahedron
IS - 13
ER -