Enantio- and Diastereoselective Synthesis of Cyclic β-Hydroxy Allylsilanes via Sequential Aldehyde γ-Silylallylboration and Ring-Closing Metathesis Reactions

Jung-Nyoung Heo; Glenn C. Micalizio; William R. Roush

doi:10.1021/ol034347t

journal article Apr 15, 2003

Enantio- and Diastereoselective Synthesis of Cyclic β-Hydroxy Allylsilanes via Sequential Aldehyde γ-Silylallylboration and Ring-Closing Metathesis Reactions

Jung-Nyoung Heo Glenn C. Micalizio William R. Roush

Organic Letters Vol. 5 No. 10 pp. 1693-1696 · American Chemical Society (ACS)

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References

37

[1]

Fleming I. Chem. Rev. (1997) 10.1021/cr941074u

[2]

For Chem. Rev. (1995) 10.1021/cr00037a008

[3]

Panek J. A. J. Am. Chem. Soc. (1991) 10.1021/ja00026a033

[4]

Panek J. A. J. Org. Chem. (1993) 10.1021/jo00056a005

[5]

Akiyama T. Tetrahedron Lett. (2001) 10.1016/s0040-4039(01)00594-9

[6]

Akiyama T. Tetrahedron Lett. (1998) 10.1016/s0040-4039(98)01748-1

[7]

Angle S. R. J. Am. Chem. Soc. (2002) 10.1021/ja012193b

[8]

Roberson C. W. J. Am. Chem. Soc. (2002) 10.1021/ja012152f

[9]

Peng Z.-H. Org. Lett. (2001) 10.1021/ol0069960

[10]

Roberson C. W. Org. Lett. (2000) 10.1021/ol9913744

[11]

Peng Z.-H. Org. Lett. (2000) 10.1021/ol005676d

[12]

Roberson C. W. J. Org. Chem. (1999) 10.1021/jo982375x

[13]

Micalizio G. C. Org. Lett. (2000) 10.1021/ol9913082

[14]

Micalizio G. C. Org. Lett. (2001) 10.1021/ol0160250

[15]

Elliot M. C. J. Chem. Soc., Perkin Trans. 1 (2001) 10.1039/b007290g

[16]

Elliot M. C. J. Chem. Soc., Perkin Trans. 1 (2000) 10.1039/a903885j

[17]

Roush W. R. Tetrahedron Lett. (2000) 10.1016/s0040-4039(00)01526-4

[18]

Fleming I. J. Chem. Soc., Perkin Trans. 1 (1992) 10.1039/p19920003331

[19]

Landais Y. Tetrahedron Lett. (2001) 10.1016/s0040-4039(01)01318-1

[20]

Roush W. R. Tetrahedron (1992) 10.1016/s0040-4020(01)88869-4

[21]

For Tetrahedron (1998) 10.1016/s0040-4020(97)10427-6

[22]

For J. Tetrahedron Lett. (1996) 10.1016/0040-4039(96)00230-4

[23]

Enantioselectivity J. Am. Chem. Soc. (1991) 10.1021/ja00011a006

[24]

Prepared J. Am. Chem. Soc. (2000) 10.1021/ja001179g

[25]

Crimmins M. T. Synth. Commun. (1998) 10.1080/00397919808004914

[26]

Clive D. L. J. J. Organomet. Chem. (1995) 10.1016/0022-328x(94)05224-y

[27]

Gu Y. G. Tetrahedron Lett. (1991) 10.1016/0040-4039(91)80678-y

[28]

Stereoselective synthesis of all four geometric isomers of internal 1,3-butadienes by the condensation reaction of aldehydes with the .gamma.-trimethylsilyl-substituted allylboranes

Kung K. Wang, Yu Gui Gu, Chin Liu

Journal of the American Chemical Society 1990 10.1021/ja00167a046

[29]

Danheiser R. L. Tetrahedron (1983) 10.1016/s0040-4020(01)88592-6

[30]

Brown H. C. J. Org. Chem. (1988) 10.1021/jo00252a032

[31]

Brown H. C. J. Am. Chem. Soc. (1985) 10.1021/ja00294a068

[32]

Roush W. (1991)

[33]

Hudrlik P. F. J. Am. Chem. Soc. (1975) 10.1021/ja00839a031

[34]

Koreeda M. J. Am. Chem. Soc. (1982) 10.1021/ja00372a034

[35]

Evans D. A. J. Am. Chem. Soc. (1982) 10.1021/ja00370a050

[36]

Lin N.-H. J. Am. Chem. Soc. (1996) 10.1021/ja961641q

[37]

Heo J.-N. Org. Lett. (2003) 10.1021/ol034349d

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Details

Published: Apr 15, 2003
Vol/Issue: 5(10)
Pages: 1693-1696

Authors

J

Jung-Nyoung Heo

Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109

G

Glenn C. Micalizio

Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109

W

William R. Roush

Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109

Cite This Article

Jung-Nyoung Heo, Glenn C. Micalizio, William R. Roush (2003). Enantio- and Diastereoselective Synthesis of Cyclic β-Hydroxy Allylsilanes via Sequential Aldehyde γ-Silylallylboration and Ring-Closing Metathesis Reactions. Organic Letters, 5(10), 1693-1696. https://doi.org/10.1021/ol034347t

Enantio- and Diastereoselective Synthesis of Cyclic β-Hydroxy Allylsilanes via Sequential Aldehyde γ-Silylallylboration and Ring-Closing Metathesis Reactions

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