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. 2008 Dec 3;130(48):16140-1.
doi: 10.1021/ja806113v.

Diastereoselective construction of functionalized homoallylic alcohols by Ni-catalyzed diboron-promoted coupling of dienes and aldehydes

Hee Yeon Cho  1 , James P Morken
Affiliations

Diastereoselective construction of functionalized homoallylic alcohols by Ni-catalyzed diboron-promoted coupling of dienes and aldehydes

Hee Yeon Cho et al. J Am Chem Soc. .

Abstract

The nickel-catalyzed reaction of carbonyls and dienes was accomplished in a regio- and stereoselective fashion employing a stoichiometric amount of bis(pinacolato)diboron. This reductive coupling furnishes an allyl boronic ester as the reaction product, a compound which was readily converted to the derived allylic alcohol by oxidative workup.

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References

    1. Marder TB, Norman NC. Topics in Catalysis. 1998;5:63.
    2. Ishiyama T, Miyaura N. J Organomet Chem. 2000;611:392.
    3. Ishiyama T, Miyaura N. Chem Record. 2004;3:271. - PubMed
    4. Beletskaya I, Moberg C. Chem Rev. 2006;106:2320. - PubMed
    5. Burks HE, Morken JP. Chem Commun. 2007:4717. - PubMed
    6. Ramirez J, Lillo V, Segarra AM, Fernandez E. Comp Rend Chim. 2007;10:138.
    1. Baker RT, Nguyen P, Marder TB, Westcott SA. Angew Chem Int Ed Engl. 1995;34:1336.
    2. Ishiyama T, Yamamoto M, Miyaura N. Chem Commun. 1997:689.
    3. Iverson CN, Smith MR., III Organometallics. 1997;16:2757.
    4. Dai C, Robins EG, Scott AJ, Clegg W, Yufit DS, Howard JAK, Marder TB. Chem Commun. 1998:1983.
    5. Nguyen P, Coapes RB, Woodward AD, Taylor NJ, Burke JM, Howard JAK, Marder TB. J Organomet Chem. 2002;652:77.
    6. Morgan JB, Miller SP, Morken JP. J Am Chem Soc. 2003;125:8702. - PubMed
    7. Trudeau S, Morgan JB, Shrestha M, Morken JP. J Org Chem. 2005;70:9538. - PubMed
    8. Ramirez J, Segarra AM, Ferandez E. Tetrahedron: Asymmetry. 2005;16:1289.
    9. Ramírez J, Corberán R, Sanaú M, Peris E, Fernandez E. Chem Commun. 2005:3056. - PubMed
    10. Lillo V, Mata J, Ramirez J, Peris E, Fernandez E. Organometallics. 2006;25:5829.
    11. Lillo V, Mas-Marzá E, Segarra AM, Carbó JJ, Bo C, Peris E, Fernandez E. Chem Commun. 2007:3380. - PubMed
    1. Ishiyama T, Yamamoto M, Miyaura N. Chem Commun. 1996:2073.
    2. Clegg W, Thorsten J, Marder TB, Norman NC, Orpen AG, Peakman TM, Quayle MJ, Rice CR, Scott AJ. J Chem Soc Dalton Trans. 1998:1431.
    3. Morgan JB, Morken JP. Org Lett. 2003;5:2573. - PubMed
    1. Ishiyama T, Kitano T, Miyaura N. Tetrahedron Lett. 1998;39:2357.
    2. Yang FY, Cheng CH. J Am Chem Soc. 2001;123:761. - PubMed
    3. Pelz NF, Woodward AR, Burks HE, Sieber JD, Morken JP. J Am Chem Soc. 2004;126:16328. - PubMed
    4. Burks HE, Liu S, Morken JP. J Am Chem Soc. 2007;129:8766. - PubMed
    1. Lawson YG, Lesley MJG, Norman NC, Rice CR, Marder TB. Chem Commun. 1997:2051.
    2. Takahashi K, Ishiyama T, Miyaura N. Chem Lett. 2000:982.
    3. Ito H, Yamanaka H, Tateiwa J, Hosomi A. Tetrahedron Lett. 2000;47:6821.
    4. Takahashi K, Ishiyama T, Miyaura N. J Organomet Chem. 2001;625:47.
    5. Kabalka GW, Das BC, Das S. Tetrahedron Lett. 2002;43:2323.
    6. Bell NJ, Cox AJ, Cameron NR, Evans JSO, Marder TB, Duin MA, Elsevier CJ, Baucherel X, Tulloch AAD, Tooze RP. Chem Commun. 2004:1854. - PubMed
    7. Ito H, Kawakami C, Sawamura M. J Am Chem Soc. 2005;127:16034. - PubMed
    8. Mun S, Lee JE, Yun J. Org Lett. 2006;8:4887. - PubMed
    9. Hirano K, Yorimitsu H, Oshima K. Org Lett. 2007;9:5031. - PubMed

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