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. 2011 Nov 4;76(21):9102-8.
doi: 10.1021/jo201321k. Epub 2011 Sep 20.

Catalytic enantioselective diboration of cyclic dienes. A modified ligand with general utility

Kai Hong  1 , James P Morken
Affiliations

Catalytic enantioselective diboration of cyclic dienes. A modified ligand with general utility

Kai Hong et al. J Org Chem. .

Abstract

The enantioselective 1,4-diboration of cyclic dienes with a new taddol-derived phosphonite ligand occurs with excellent enantioselectivity. Oxidation delivers the derived 1,4-diol, whereas homologation can be used to deliver a chiral 1,6-diol.

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Figures

Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
See this image and copyright information in PMC

References

    1. Burks HE, Kliman LT, Morken JP. J Am Chem Soc. 2009;131:9134. - PMC - PubMed

    1. Non-enantioselective diene diboration: Ishiyama T, Yamamoto M, Miyaura N. Chem Commun. 1996:2073.Ishiyama T, Yamamoto M, Miyaura N. Chem Commun. 1997:689.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.Morgan JB, Morken JP. Org Lett. 2003;5:2573.

    1. Recent reviews: Burks HE, Morken JP. Chem Commun. 2007:4717.Ramirez J, Lillo V, Segarra AM, Fernandez E. Comp Rend Chim. 2007;10:138.Beletskaya I, Moberg C. Chem Rev. 2006;106:2320.Ishiyama T, Miyaura N. Chem Record. 2004;3:271.Marder TB, Norman NC. Topics in Catalysis. 1998;5:63.

    1. 1,4-Dihydroxylation of dienes, and related reactions, have been accomplished, in moderate selectivity, under Pd-catalyzed oxidative conditions, see: Thorarensen A, Palmgren A, Itami K, Bäckvall JE. Tetrahedron Lett. 1997;38:8541.Itami K, Palmgren A, Thorarensen A, Bäckvall JE. J Org Chem. 1998;63:6466.Verboom RC, Plietker BJ, Bäckvall JE. J Organomet Chem. 2003;687:508.El-Qisairi AK, Qaseer HA, Fennelly JP, Chiarelli MP, Henry PM. Catalysis Commun. 2008;9:1661.

    1. For a review of these ligands in asymmetric catalysis, see: Lam HW. Synthesis. 2011:2011.For selected primary references, see: Sakaki J, Schweizer WB, Seebach D. Helv Chem Acta. 1993;76:2654.Seebach D, Hayakawa M, Sakaki J, Schweizer WB. Tetrahedron. 1993;49:1711.Alexakis A, Burton J, Vastra J, Benhaim C, Fournioux X, van den Heuvel A, Leveque JM, Maze F, Rosset S. European Journal of Organic Chemistry. 2000:4011.Bee C, Han SB, Hassan A, Iida H, Krische MJ. J Am Chem Soc. 2008;130:2746.

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