ORGANIC
LETTERS
2006
Vol. 8, No. 8
1629-1632
Stereoselective Synthesis of Protected
1,2-Diols and 1,2,3-Triols by a Tandem
Hydroboration−Coupling Sequence
Manmohan Kapur, Anton Khartulyari, and Martin E. Maier*
Institut fu¨r Organische Chemie, UniVersita¨t Tu¨bingen, Auf der Morgenstelle 18,
D-72076 Tu¨bingen, Germany
Received January 25, 2006
ABSTRACT
A new approach to complex chiral diols and polyols is described utilizing a tandem hydroboration/Suzuki cross-coupling reaction. This method
utilizes the versatility of a glycolate-derived chiral template.
Clusters of two or more vicinal hydroxyl groups are
frequently found in natural products. Examples include
carbohydrates and some macrolides. Because of the impor-
tance of 1,2-diols and 1,2,3-triols, a range of methods have
been developed for their synthesis. For example, carbon-
carbon bond-forming reactions on suitable substrates can be
used. Thus, aldol reactions,1 addition reactions to R-hydroxy
aldehydes,2 Pinacol couplings,3 or epoxide opening reactions4
have been employed in this context. In addition, carbon-
oxygen bond forming reactions such as epoxidation5,6 or
dihydroxylation7 are valuable options. However, the famous
Sharpless asymmetric dihydroxylation is less suitable for the
synthesis of anti- and 1,2-diols. Finally, carbon-hydrogen
bond forming reactions (reductions) on carbonyl-containing
substrates can be considered. The choice of a certain strategy
is largely governed by other groups in the near or somewhat
remote vicinity of the diol.
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558. (c) Evans, D. A.; Gage, J. R.; Leighton, J. L.; Kim, A. S. J. Org.
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G.; List, B.; Shabat, D.; Anderson, J.; Gramatikova, S.; Lerner, R. A.;
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K. Liebigs Ann. Chem. 1988, 209-214. (f) Takenaka, N.; Xia, G.;
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(4) Boeckman, R. K., Jr.; Liu, X. Synthesis 2002, 2138-2142.
(5) Shi, Y. Acc. Chem. Res. 2004, 37, 488-496.
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357-398.
10.1021/ol0602194 CCC: $33.50
© 2006 American Chemical Society
Published on Web 03/14/2006