Received 29 August 2012
aDepartment of Chemistry, Faculty of Science and Technology, University of Tromsø, N-9037 Tromsø, Norway, and bX-ray Structural Centre, A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street B-334, Moscow 119991, Russian Federation
Correspondence e-mail: email@example.com
The molecule of the title compound, C16H21BO2, comprises a chiral fused tricyclic system containing five-membered (1,3,2-dioxaborolane), six-membered (cyclohexane) and four-membered (cyclobutane) rings. The 1,3,2-dioxaborolane ring is almost planar (r.m.s. deviation = 0.035 Å), and the syn H and Me substituents at this ring are in an eclipsed conformation. The cyclohexane and cyclobutane rings adopt sofa and butterfly conformations, respectively. The B atom has a trigonal-planar configuration (sum of the bond angles = 360.0°). The phenyl ring is practically coplanar with the 1,3,2-dioxaborolane ring [dihedral angle between the ring planes = 1.96 (8)°]. The absolute structure was determined from the known configuration of (+)-pinanediol which was used in the synthesis. In the crystal, weak C-H(Ph) interactions occur.
For the Matteson homologation reaction, see: Matteson et al. (1983); Matteson (1989). For 2-substituted (+)-pinanediolboronates, see: Carmès et al. (2000); Caselli et al. (2003); Morandi et al. (2003, 2005).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2267 ).
The Norwegian Research Council is acknowledged for research grant 166742.
Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS, Madison, Wisconsin, USA.
Carmès, L., Carreaux, F. & Carboni, B. (2000). J. Org. Chem. 65, 5403-5408.
Caselli, E., Danieli, C., Morandi, S., Bonfiglio, B., Forni, A. & Prati, F. (2003). Org. Lett. 5, 4863-4866.
Matteson, D. S. (1989). Chem. Rev. 89, 1535-1551.
Matteson, D. S., Ray, R., Rocks, R. R. & Tsai, D. J. S. (1983). Organometallics, 2, 1536-1543.
Morandi, S., Caselli, E., Forni, A., Bucciarelli, M., Torre, G. & Prati, F. (2005). Tetrahedron Asymmetry, 16, 2918-2926.
Morandi, F., Caselli, E., Morandi, S., Focia, P. J., Blásquez, J., Shoichet, B. K. & Prati, F. (2003). J. Am. Chem. Soc. 125, 685-695.
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.