74672-06-3Relevant academic research and scientific papers
Introduction of Cyclopropyl and Cyclobutyl Ring on Alkyl Iodides through Cobalt-Catalyzed Cross-Coupling
Andersen, Claire,Ferey, Vincent,Daumas, Marc,Bernardelli, Patrick,Guérinot, Amandine,Cossy, Janine
, p. 2285 - 2289 (2019/03/29)
A cobalt-catalyzed cross-coupling between alkyl iodides and cyclopropyl, cyclobutyl, and alkenyl Grignard reagents is disclosed. The reaction allows the introduction of strained rings on a large panel of primary and secondary alkyl iodides. The catalytic system is simple and nonexpensive, and the reaction is general, chemoselective, and diastereoconvergent. The alkene resulting from the cross-coupling can be transformed to substituted cyclopropanes using a Simmons-Smith reaction. The formation of radical intermediates during the coupling is hypothesized.
An efficient asymmetric synthesis of key intermediates in the synthesis of aphanorphine and eptazocine
Taylor, Stephen K.,Ivanovic, Milica,Simons, Lloyd J.,Davis, Matthew M.
, p. 743 - 747 (2007/10/03)
Efficient, formal syntheses of aphanorphine and eptazocine are reported that involve epoxide cyclizations. The necessary chiral epoxides were prepared following treatment of diols prepared by Sharpless asymmetric osmylations of an alkene. The cyclizations formed a ring compound with the same enantiomeric purity as the starting epoxide.
Addition of Organozinc Compounds to C=C-Bonds, III. --- Addition of Bis(2-methylallyl)zinc to para- and meta- Substituted Styrenes
Lehmkuhl, Herbert,McLane, Raymond
, p. 736 - 743 (2007/10/02)
A Hammett correlation between the ratio of M --> Cprim/M --> Csec addition and the substituent constants ?+ has been found for the addition of bis(2-methylallyl)zinc (1) to p- and m-substituted styrenes 2-8.Electron donating substituents favour M --> Cprim addition, electron withdrawing substituents M --> Csec addition.
