127041-68-3Relevant articles and documents
A practical route to enantiopure 3-hydroxy-pyrrolidines: application to a straightforward synthesis of (-)-bulgecinine
Toumi, Mathieu,Couty, Fran?ois,Evano, Gwilherm
, p. 1175 - 1179 (2008/09/18)
A practical synthesis of enantiopure substituted 3-hydroxy-pyrrolidines is reported. In four steps, starting from commercially available amino acids as chiral educts, this method allows for an efficient preparation of a variety of 3-hydroxy-pyrrolidines, as well as 3-hydroxy-piperidines and azepanes. Application of this methodology for a straightforward asymmetric synthesis of (-)-bulgecinine is also described.
The stereochemical course of addition of allyltrimethylsilane to protected L-alaninals and L-serinals in the presence of Lewis acids. Total synthesis of cis-(2R,3S)-3-hydroxyproline
Gryko,Prokopowicz,Jurczak
, p. 1103 - 1113 (2007/10/03)
The influence of Lewis acids on the diastereoselectivity of the addition of allyltrimethylsilane to variously protected L-alaninals and L-serinals was investigated and high levels of asymmetric induction were achieved. Stereochemical models for rationalisation of the results obtained are proposed. cis-(2R,3S)-3-Hydroxyproline was synthesised starting from N-Cbz, O-TBS-L-serinal, in which the crucial step involves addition of allyltrimethylsilane to the aldehyde in the presence of SnCl4.
A Novel BF3*OEt2-Catalyzed Annulation of N-Cbz-α-Amino Aldehides with Allyltrimethylsilane. Highly Stereoselective Synthesis of Cis-2,3,5-Trisubstituted Pyrrolidines
Kiyooka, Syun-ichi,Shiomi, Yasuhiro,Kira, Haruhide,Kaneko, Yuichi,Tanimori, Shinji
, p. 1958 - 1960 (2007/10/02)
In the presence of BF3*OEt2 (0.2 molar equiv), the reactions (-10 deg C, CH2Cl2) of N-Cbz-α-amino aldehydes with allyltrimethylsilane produced pyrrolidines in good yields (70-80percent), with high all-cis stereoselectivity at the C-2, C-3, and C-5 positio
