119645-17-9Relevant academic research and scientific papers
Stereodivergent synthesis of the enolates of a β-amino ester by using lithium N-benzyltrimethylsilylamide
Asao, Naoki,Uyehara, Tadao,Yamamoto, Yoshinori
, p. 4563 - 4572 (2007/10/02)
Highly stereoselective generation of both Z- and E-enolates (1 and 3)2 is accomplished by the conjugate addition of lithium N-benzyltrimethylsilylamide (LSA) to methyl crotonate. The alkylation with alkyl halides and aldol condensation with aldehydes via 1 and 3 are studied. The alkylation of 3 produces moderate to good syn selectivity, while that of 1 gives no selectivity. The aldol condensation of 1 affords the anti-syn isomer (11) predominantly, whereas that of 3 gives the syn-anti isomer (14) preferentially.
Highly Stereodivergent Generation of the Z- and E-Enolates of a β-Amino Ester via Conjugate Addition to Methyl Crotonate by using Lithium N-Benzyltrimethylsilylamide as a Nitrogen Nucleophile, and Application to Stereoselective Aldol Reactions
Uyehara, Tadao,Asao, Naoki,Yamamoto, Yoshinori
, p. 753 - 754 (2007/10/02)
Methods for highly stereoselective generation of both Z- and E-enolates of a β-amino ester have been developed on the basis of conjugate addition of lithium N-benzyltrimethylsilylamide to methyl crotonate and applied to stereoselective synthesis of anti,syn- and syn,anti-β-amino-β'-hydroxy esters by treatment with aldehyde.
LITHIUM N-BENZYLTRIMETHYLSILYLAMIDE (LSA): A NEW REAGENT FOR CONJUGATE ADDITION - ENOLATE TRAPPING REACTIONS
Asao, Naoki,Uyehara, Tadao,Yamamoto, Yoshinori
, p. 4173 - 4180 (2007/10/02)
Lithium N-benzyltrimethylsilylamide (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 conjugat
