100937-47-1Relevant articles and documents
Asymmetric Catalytic Reduction of meso-Imides
Kang, Jahyo,Lee, Jun Won,Kim, Joo In,Pyun, Chongsuh
, p. 4265 - 4268 (1995)
A thiazazincolidine complex, 1, was shown to be an excellent catalyst for enantioselective reduction with bis(2,6-dimethylphenoxy)borane (BDMPB) of meso N-phenylimides in high ee to the corresponding hydroxy lactams, which were eventually converted to the corresponding lactones of high optical purity.
Catalytic asymmetric oxidative lactonizations of meso-diols using a chiral iridium complex
Suzuki, Takeyuki,Morita, Kenji,Matsuo, Yoshimi,Hiroi, Kunio
, p. 2003 - 2006 (2007/10/03)
A chiral amino alcohol/Ir complex catalyzes the asymmetric oxidative lactonizations of meso-diols to give the corresponding lactones in up to 81% ee.
Enantioselective reduction of meso-cyclic-1,2-dicarboxylic anhydrides and 1,2-dicarboximides: Asymmetric synthesis of bicyclic lactones and hydroxylactams
Matsuki,Inoue,Ishida,Takeda,Nakagawa,Hino
, p. 9 - 18 (2007/10/02)
Chiral bicyclic lactones (3,8,9) and bicyclic hydroxylactams (10-13) were synthesized by highly enantioselective reduction of meso-cyclic-1,2- dicarboxylic anhydrides (1, 4) and meso-cyclic-1,2-dicarboximides (2) with lithium aluminum hydride (LiAlH4)-alcohol(ROH)-(R)- or (S)-1,1'-bi-2- naphthol complex [(R)- or (S)-BINAL-H(ROH)]. Treatment of the hydroxylactams (10-13) with triethylsilane (Et3SiH) and trifluoroacetic acid (CF3CO2H) gave chiral bicyclic lactams (14, 15) in quantitative yields. Removal of the N-4-methoxyphenyl group of the lactams (14, 15) with cerium(IV) ammonium nitrate (CAN) proceeded smoothly to give the corresponding N-unsubstituted lactams (16, 17) in high optical purity.