Chiral Sulfides for Optically Active Three-membered Rings

Isothiocineoles (1, 2) are limonene derivatives and useful chiral auxiliaries for the synthesis of optically active epoxides, aziridines¹⁾ and cyclopropanes.²⁾ For instance, a sulfur ylide 3, derived from 1, reacts with aldehydes and tosylimides to afford chiral epoxides and aziridines, respectively, in high diastereo- and enantioselectivity. It is found that this asymmetric reaction can smoothly proceed on gram scale. Furthermore, asymmetric syntheses of quinine and quinidine has been reported, in which this epoxidation was used as a key reaction.¹⁾ Another advantage is that 1 and 2 can be recovered and recycled after the reaction.

Related Products

T2578

(-)-Isothiocineole

T2579

(+)-Isothiocineole

References

• 1) Practical and Highly Selective Sulfur Ylide Mediated Asymmetric Epoxidations and Aziridinations Using an Inexpensive, Readily Available Chiral Sulfide. Applications to the Synthesis of Quinine and Quinidine
  • O. Illa, M. Arshad, A. Ros, E. M. McGarrigle, V. K. Aggarwal, J. Am. Chem. Soc. 2010, 132, 1828.
• 2) Asymmetric synthesis of cyclopropyl phosphonates using chiral terpenyl sulfonium and selenonium ylides
  • W. H. Midura, J. Ścianowski, A. Banach, A. Zając, Tetrahedron Asymmetry 2014, 25, 1488.

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