Tetrahedron

Synthesis of the enantiomers of cis-2-methyl-5-hexanolide, the major component of the sex pheromone of the carpenter bee

K Mori, S Senda

Index: Mori, Kenji; Senda, Shuji Tetrahedron, 1985 , vol. 41, # 3 p. 541 - 546

Full Text: HTML

Citation Number: 56

Abstract

(2R, 5S)-2-Methyl-5-hexanolide and its antipode were synthesized in highly optically pure state (⩾ 98–99% ee) starting from ethyl (S)-lactate and the enantiomers of methyl β- hydroxyisobutyrate. The specific rotations of our samples were [α] D±91.0-93.5°(CHCl3), while the reported values of the samples prepared by resolution or asymmetric synthesis were±64.5–65.6°.

Related Articles:

Enantioselective polymerization of epoxides: a highly active and selective catalyst for the preparation of stereoregular polyethers and enantiopure epoxides

[Hirahata, Wataru; Thomas, Renee M.; Lobkovsky, Emil B.; Coates, Geoffrey W. Journal of the American Chemical Society, 2008 , vol. 130, # 52 p. 17658 - 17659]

Asymmetric epoxidation of terminal alkenes with hydrogen peroxide catalyzed by pentafluorophenyl PtII complexes

[Journal of the American Chemical Society, , vol. 128, # 43 p. 14006 - 14007]

Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen) CoIII complexes. Practical synthesis of enantioenriched terminal epoxides …

[Journal of the American Chemical Society, , vol. 124, # 7 p. 1307 - 1315]

Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen) CoIII complexes. Practical synthesis of enantioenriched terminal epoxides …

[Schaus, Scott E.; Brandes, Bridget D.; Larrow, Jay F.; Tokunaga, Makoto; Hansen, Karl B.; Gould, Alexandra E.; Furrow, Michael E.; Jacobsen, Eric N. Journal of the American Chemical Society, 2002 , vol. 124, # 7 p. 1307 - 1315]

A new dinuclear chiral salen complexes for asymmetric ring opening and closing reactions: Synthesis of valuable chiral intermediates

[Thakur, Santosh Singh; Chen, Shu-Wei; Li, Wenji; Shin, Chang-Kyo; Kim, Seong-Jin; Koo, Yoon-Mo; Kim, Geon-Joong Journal of Organometallic Chemistry, 2006 , vol. 691, # 9 p. 1862 - 1872]

More Articles...