Radical Cyclization in the Control of Regio- and Stereochemistry
作者： Gilbert Stork
DOI: 10.1246/BCSJ.61.149
关键词: Double bond 、 Stereospecificity 、 Stereoselectivity 、 Regioselectivity 、 Steroid 、 Stereochemistry 、 Radical cyclization 、 Ether 、 Chemistry 、 Acetal 、 General chemistry
摘要: This article presents a review of the control regio- and stereochemistry which is now possible by use recently introduced haloacetal related halosilyl ether cyclizations, starting from cyclohexenol or cyclopentenol. The hydroxyl group element permits addition two carbon chains to double bond allylic alcohol system, with complete regiospecificity stereospecificity at near end bond, high stereoselectivity far bond. Examples new methodology field alkaloid, steroid prostaglandin synthesis are given.
csj.jp参考文章(17)
Kohei Tamao, Neyoshi Ishida, Makoto Kumada, (Diisopropoxymethylsilyl)methyl Grignard reagent: a new, practically useful nucleophilic hydroxymethylating agent Journal of Organic Chemistry. ,vol. 14, pp. 2120- 2122 ,(1983) , 10.1021/JO00160A046
Gilbert Stork, Michael Kahn, Control of ring junction stereochemistry via radical cyclization Journal of the American Chemical Society. ,vol. 107, pp. 500- 501 ,(1985) , 10.1021/JA00288A038
Gilbert. Stork, Philip Michael. Sher, Hai Lin. Chen, Radical cyclization-trapping in the synthesis of natural products. A simple, stereocontrolled route to prostaglandin F2.alpha. Journal of the American Chemical Society. ,vol. 108, pp. 6384- 6385 ,(1986) , 10.1021/JA00280A043
Cheves Walling, Angela Cioffari, Cyclization of 5-hexenyl radicals Journal of the American Chemical Society. ,vol. 94, pp. 6059- 6064 ,(1972) , 10.1021/JA00772A020
Gilbert Stork, Robert Mook, Vinyl radical cyclizations mediated by the addition of stannyl radicals to triple bonds Journal of the American Chemical Society. ,vol. 109, pp. 2829- 2831 ,(1987) , 10.1021/JA00243A049
Kendall N. Houk, Michael N. Paddon-Row, D. C. Spellmeyer, Nelson G. Rondan, Shigeru Nagase, Theoretical transition structures for radical additions to alkenes Journal of Organic Chemistry. ,vol. 51, pp. 2874- 2879 ,(1986) , 10.1021/JO00365A004
G. Stork, Philip Michael Sher, Regiospecific trapping of radicals from cyclization reactions. Cyclic nitriles via isocyanide trapping Journal of the American Chemical Society. ,vol. 105, pp. 6765- 6766 ,(1983) , 10.1021/JA00360A062
Athelstan L.J. Beckwith, Carl H. Schiesser, Regio- and stereo-selectivity of alkenyl radical ring closure: a theoretical study Tetrahedron. ,vol. 41, pp. 3925- 3941 ,(1985) , 10.1016/S0040-4020(01)97174-1
H.B. B:urgi, J.D. Dunitz, J.M. Lehn, G. Wipff, Stereochemistry of reaction paths at carbonyl centres Tetrahedron. ,vol. 30, pp. 1563- 1572 ,(1974) , 10.1016/S0040-4020(01)90678-7
Gilbert. Stork, Philip Michael. Sher, A catalytic tin system for trapping of radicals from cyclization reactions. Regio- and stereocontrolled formation of two adjacent chiral centers Journal of the American Chemical Society. ,vol. 108, pp. 303- 304 ,(1986) , 10.1021/JA00262A024