Two-step, Stereoselective Synthesis of Linalyl Oxides by Asymmetric Allylic O-alkylation

Authors

Kanny K. Wan '11, Harvey Mudd College
Jonathan P. Litz '09, Harvey Mudd College
David A. Vosburg, Harvey Mudd CollegeFollow

Student Co-author

HMC Undergraduate

Document Type

Article

Department

Chemistry (HMC)

Publication Date

2010

Abstract

Each of the four tetrahydrofuran linalyl oxides was prepared by a Sharpless asymmetric dihydroxylation of geranyl acetate with AD-mix-α or AD-mix-β, followed by a stereoselective palladium-mediated cyclization using the chiral ligand C₃-TunePhos.

Rights Information

© 2010 Elsevier Ltd.

DOI

10.1016/j.tetasy.2010.08.011

Recommended Citation

Kanny K. Wan, Jonathan P. Litz, David A. Vosburg, Two-step, stereoselective synthesis of linalyl oxides by asymmetric allylic O-alkylation, Tetrahedron: Asymmetry, Volume 21, Issue 19, 7 October 2010, Pages 2425-2428, ISSN 0957-4166, http://dx.doi.org/10.1016/j.tetasy.2010.08.011. (http://www.sciencedirect.com/science/article/pii/S0957416610006464)