Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the linalool route

作者: Giovanni Vidari , Anna Di Rosa , Giuseppe Zanoni , Carlo Bicchi

DOI: 10.1016/S0957-4166(99)00359-6

关键词: TetrahydropyranAllylic alcoholLinaloolStereoselectivityOrganic chemistryDihydroxylationStereochemistryEnantioselective synthesisChemistry

摘要: Abstract Each of the four enantiomerically pure tetrahydropyran linalool oxides was prepared by separate enantioselective Sharpless dihydroxylation (R)- or (S)-linalyl acetate with AD-mix-α AD-mix-β, followed a completely stereoselective N-phenylselenophthalimide cyclization an intermediate allylic alcohol.

参考文章(42)
Roy A. Johnson, K. Barry Sharpless, Addition Reactions with Formation of Carbon–Oxygen Bonds: (ii) Asymmetric Methods of Epoxidation Comprehensive Organic Synthesis. ,vol. 3, pp. 389- 436 ,(1991) , 10.1016/B978-0-08-052349-1.00196-7
Mitsuo Miyazawa, Katsuyuki Yokote, Hiromu Kameoka, RESOLUTION OF RACEMIC LINALOOL OXIDE-PYRANOID BY MICROBIAL ESTERIFICATION Tetrahedron-asymmetry. ,vol. 6, pp. 1067- 1068 ,(1995) , 10.1016/0957-4166(95)00126-A
J.G. Urones, P. Basabe, I.S. Marcos, J. Pineda, A.M. Lithgow, R.F. Moro, F.M.S. Brito Palma, M.E.M. Arau´jo, M.D.G. Gravalos, Meroterpenes fromCystoseira usneoides Phytochemistry. ,vol. 31, pp. 179- 182 ,(1992) , 10.1016/0031-9422(91)83031-F
Robert M. Scarborough, Amos B. Smith, W. E. Barnette, K Nicolaou, Organoselenium-induced ring closures: cyclization of dienes with "PhSeOH" to form cyclic ethers Journal of Organic Chemistry. ,vol. 10, pp. 1742- 1744 ,(1979) , 10.1021/JO01324A046
Anna-Karin Borg-Karlson, C.Rikard Unelius, Irena Valterová, L. Anders Nilsson, Floral fragrance chemistry in the early flowering shrub Daphne mezereum Phytochemistry. ,vol. 41, pp. 1477- 1483 ,(1996) , 10.1016/0031-9422(95)00801-2
Rosa L. Dorta, María S. Rodríguez, JoséA. Salazar, Ernesto Suárez, 1,3-Transposition of primary allylic alcohols: Synthesis of optically active secondary and tertiary allylic alcohols Tetrahedron Letters. ,vol. 38, pp. 4675- 4678 ,(1997) , 10.1016/S0040-4039(97)00964-7
A. Corma, M. Iglesias, F. Sánchez, Large pore bifunctional titanium–aluminosilicates: the inorganic non-enzymatic version of the epoxidase conversion of linalool to cyclic ethers Journal of The Chemical Society, Chemical Communications. pp. 1635- 1636 ,(1995) , 10.1039/C39950001635
Chris A. Broka, Yi Tsong Lin, Synthetic studies on thyrsiferol. Elaboration of the bromotetrahydropyran ring Journal of Organic Chemistry. ,vol. 53, pp. 5876- 5885 ,(1988) , 10.1021/JO00260A016
Satoru Masamune, William Choy, John S. Petersen, Lawrence R. Sita, Double Asymmetric Synthesis and a New Strategy for Stereochemical Control in Organic Synthesis Angewandte Chemie. ,vol. 24, pp. 1- 30 ,(1985) , 10.1002/ANIE.198500013