6.16 Functional Group Transformation via Allyl Rearrangement

作者: Z. Gu , A. Zakarian

DOI: 10.1016/B978-0-08-097742-3.00624-8

关键词:

摘要: This chapter describes recent developments in the versatile and multifaceted chemistry of allylic transposition reactions, concentrating on contributions reported past decade. In beginning chapter, authors describe a variety mechanistic pathways by which substitution reactions occur, including nucleophilic, electrophilic, radical, organometallic, concerted pericyclic processes. discussion is followed examples representative with preference for products based identity leaving incoming atoms newly installed group. The are broadly grouped into heteroatom transpositions heteroatom-to-carbon transpositions. As evident from presented material, astonishingly rich will continue to be foundation development powerful innovative chemical methodology.

参考文章(655)
S. Swaminathan, K.G. Srinivasan, P.S. Venkataramani, Rearrangements of bicyclic-δ-hydroxy-α,β-enones—IV Tetrahedron. ,vol. 26, pp. 1453- 1461 ,(1970) , 10.1016/S0040-4020(01)92974-6
Anthony Cunningham, Vijaya Mokal-Parekh, Claire Wilson, Simon Woodward, On the use of mixtures of organotin species for catalytic enantioselective ketone allylation—a detective story Org. Biomol. Chem.. ,vol. 2, pp. 741- 748 ,(2004) , 10.1039/B313384B
Jason W. J. Kennedy, Dennis G. Hall, Dramatic rate enhancement with preservation of stereospecificity in the first metal-catalyzed additions of allylboronates. Journal of the American Chemical Society. ,vol. 124, pp. 11586- 11587 ,(2002) , 10.1021/JA027453J
Barry M. Trost, Hong C. Shen, Li Dong, Jean-Philippe Surivet, Catherine Sylvain, Synthesis of chiral chromans by the Pd-catalyzed asymmetric allylic alkylation (AAA): scope, mechanism, and applications. Journal of the American Chemical Society. ,vol. 126, pp. 11966- 11983 ,(2004) , 10.1021/JA048078T
John A. Enquist Jr, Brian M. Stoltz, The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation Nature. ,vol. 453, pp. 1228- 1231 ,(2008) , 10.1038/NATURE07046
Gregory R. Cook, Robert Kargbo, Bikash Maity, Catalytic enantioselective indium-mediated allylation of hydrazones. Organic Letters. ,vol. 7, pp. 2767- 2770 ,(2005) , 10.1021/OL051160O
Todd K. Macklin, Glenn C. Micalizio, Total synthesis and structure elucidation of (+)-phorbasin C. Journal of the American Chemical Society. ,vol. 131, pp. 1392- 1393 ,(2009) , 10.1021/JA809491B
Jason A. Mulder, Richard P. Hsung, Michael O. Frederick, Michael R. Tracey, Craig A. Zificsak, The first stereoselective Ficini-Claisen rearrangement using chiral ynamides. Organic Letters. ,vol. 4, pp. 1383- 1386 ,(2002) , 10.1021/OL020037J
Ian Fleming, Jennifer A. Langley, The mechanism of the protodesilylation of allylsilanes and vinylsilanes Journal of the Chemical Society, Perkin Transactions 1. ,vol. 12, pp. 1421- 1423 ,(1981) , 10.1039/P19810001421