Intramolecular hydrosilylation and silicon-assisted cross-coupling: An efficient route to trisubstituted homoallylic alcohols

Organic Letters

Volumn 3, Issue 1, 2001, Pages 61-64

  Denmark, Scott E ^a   Weitao, Pan ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

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EID: 0001769585     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006769y     Document Type: Article

References (24)

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3. (a) Hatanaka, Y.; Hiyama, T. Synlett 1991, 845.
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15. For an excellent review of hydrosilylation, see: Ojima, I.; Li, Z.; Zhu, J. In The chemistry of organic silicon compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons: Great Britain, 1998; Vol. 2; pp 1687-1792.
16. For a single previous example of this concept see ref 3a.
17. We ascribe this to the strain of the silacyclopentane ring and the low energy barrier to silyl ether exchange.
18. Without removing the TMDS, the reaction gave a 63% yield of the product (72% conversion) over 44 h on a small scale, with 10 mol % catalyst loading.
19. It is conceivable that a competitive intermolecular hydrosilylation competes to form the undesired isomer.
20. See the following and references therein: (a) Takeda, T.; Kabasawa, Y.; Fujiwara, T. Tetrahedron 1995, 51, 2515.
21. (b) Okuma, K.; Tanaka, Y.-i; Hirabayashi, S.-i; Shiqji, K.; Matsuyama, H. Hereocycles 1997, 45, 1385.
22. (c) Crousse, B.; Alami, M.; Linstrumelle, G. Synlett 1997, 922.
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24. (b) Tamao, K.; Maeda K.; Tanaka, T.; Ito, Y. Tetrahedron Lett. 1988, 29, 6955.