129380-08-1Relevant academic research and scientific papers
Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: Application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes
Saravanan,Bisai, Alakesh,Baktharaman,Chandrasekhar,Singh, Vinod K
, p. 4693 - 4706 (2007/10/03)
A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides. The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product.
An efficient synthesis of chiral nonracemic diamines: Application in asymmetric synthesis
Saravanan, Parthasarathy,Singh, Vinod K.
, p. 167 - 170 (2007/10/03)
A variety of chiral diamines have been synthesized from optically active mandelic acid in an efficient manner. The chiral nonracemic lithium amide base derived from one of the diamines has been used in formal asymmetric synthesis of natural products such as (-)-utenone A and (-)-carbovir.
Enantioselective conjugate addition to cyclic enones with scalemic lithium organo(amido)cuprates, part IV. Relationship between ligand structure and enantioselectivity
Rossiter, Bryant E.,Eguchi, Masakatsu,Miao, Guobin,Swingle, Nicole M.,Hernandez, Amelia E.,Vickers, Denise,Fluckiger, Ezdan,Greg Patterson,Vasavi Reddy
, p. 965 - 986 (2007/10/02)
Scalemic lithium amides derived from primary and secondary amines react with organocopper compounds in ether or dimethyl sulfide to form lithium organo(amido)cuprates capable of enantioselective conjugate addition to 2-cycloalkenones. The most successful heterocuprate, in which the chiral ligand is (S)-N-methyl-1-phenyl-2-(1-piperidinyl)ethanamine, (S)-MAPP, 13, reacts with cyclic enones to form products with up to 97% ee. Nonlinear asymmetric induction was observed with the cuprate formed from ligand 13.
ENANTIOSELECTIVE CONJUGATE ADDITION TO CYCLIC ENONES WITH (S)-MAPP-CUPRATES
Rossiter, Bryant E.,Eguchi, Masakatsu,Hernandez, Amelia E.,Vickers, Denise,Medich, John,et al.
, p. 3973 - 3976 (2007/10/02)
Chiral amidocuprates, formed from CuI, n-butyl or methyl lithium and (S)-N-methyl-1-phenyl-2-(1-piperidinyl)ethanamine, (S)-MAPP, react enantioselectively with 5, 6, 7 and 8-membered cyclic enones to give products with up to 97percent e.e.The synthesis of (S)-MAPP is also reported.
