1072028-50-2Relevant articles and documents
Stereoselective Total Synthesis of (-)-(2 S,4 R)-3′-Methoxyl Citreochlorol: Preparation and Use of New Proline-Based Auxiliary for Asymmetric Acetate Aldol Reaction
Sunnapu, Ranganayakulu,Banoth, Saikumar Naik,Reyno,Thomas, Aleena,Venugopal, Navyasree,Rajendar, Goreti
, p. 4103 - 4113 (2020/03/05)
The first stereoselective total synthesis of (-)-(2S,4R)-3′-methoxy citreochlorol and (-)-(2S,4S)-3′-methoxy citreochlorol is demonstrated. A proline-based imidazolidinone was synthesized and used as chiral auxiliary for asymmetric acetate aldol reaction to generate initial chirality in the targeted molecule. Geminal dichloromethane functionality was introduced by the addition of in situ generated dichloromethyllithium to Weinreb's amide functional group.
Protective group-free synthesis of new chiral diamines via direct azidation of 1,1-diaryl-2-aminoethanols
Roy, Harendra Nath,Pitchaiah, Arigala,Kim, Miri,Hwang, In Taek,Lee, Kee-In
, p. 3526 - 3530 (2013/04/10)
A direct azidation of tertiary alcohols using sodium azide-sulfuric acid is described; the present method provides an efficient and practical path for the synthesis of new chiral diamines from unmasked 1,1-diaryl-2-aminoethanols derived from natural amino
Synthesis of chiral 2-(anilinophenylmethyl)pyrrolidines and 2-(anilinodiphenylmethyl)pyrrolidine and their application to enantioselective borane reduction of prochiral ketones as chiral catalysts
Hosoda, Naoya,Kamito, Hideaki,Takano, Miki,Takebe, Yoshitaka,Yamaguchi, Yoshitaka,Asami, Masatoshi
, p. 1739 - 1746 (2013/03/13)
Chiral diamines, 2-(anilinophenylmethyl)pyrrolidines and 2-(anilinodiphenylmethyl)pyrrolidine, were prepared from N-(tert-butoxycarbonyl) pyrrolidine or (S)-proline as a starting material, respectively. These chiral diamines were efficient for the catalytic enantioselective borane reduction of acetophenone. Using (S)-2-(anilinodiphenylmethyl)pyrrolidine, chiral secondary alcohols were obtained from prochiral ketones with good to excellent enantiomeric excesses (up to 98% ee).