383127-36-4Relevant articles and documents
Enantioconvergent cross-couplings of racemic alkylmetal reagents with unactivated secondary alkyl electrophiles: Catalytic asymmetric Negishi α-alkylations of N-Boc-pyrrolidine
Cordier, Christopher J.,Lundgren, Rylan J.,Fu, Gregory C.
supporting information, p. 10946 - 10949 (2013/08/23)
Although enantioconvergent alkyl-alkyl couplings of racemic electrophiles have been developed, there have been no reports of the corresponding reactions of racemic nucleophiles. Herein we describe Negishi cross-couplings of racemic α-zincated N-Boc-pyrrolidine with unactivated secondary halides, thus providing a one-pot, catalytic asymmetric method for the synthesis of a range of 2-alkylpyrrolidines (an important family of target molecules) from N-Boc-pyrrolidine, a commercially available precursor. Preliminary mechanistic studies indicated that two of the most straightforward mechanisms for enantioconvergence (dynamic kinetic resolution of the organometallic coupling partner and a simple β-hydride elimination/β-migratory insertion pathway) are unlikely to be operative.
A Simple Asymmetric Synthesis of 2-Substituted Pyrrolidines and 5-Substituted Pyrrolidinones
Burgess, Laurence E.,Meyers, A. I.
, p. 1656 - 1662 (2007/10/02)
An efficient procedure for the preparation of the title compounds in high enantiomeric purity has been realized starting from 3-acylpropionic acids.Stereoselective reduction of chiral bicyclic lactams 2a-h, prepared from the corresponding γ-keto acid and
A Simple Asymmetric Synthesis of 2-Substituted Pyrrolidines from 3-Acylpropionic Acids
Meyers, A. I.,Burgess, Laurence E.
, p. 2294 - 2296 (2007/10/02)
The title compounds have been prepared from 3-acylpropionic acids 2 and (-)-R-phenylglycinol in a three-step sequence in >98percent enantiomeric excess.The R group in 2 ultimately becomes the 2-substituent in the chiral pyrrolidine.