Diisopinocampheylborane
UPAC name : bis {(1S,2S,3S,5R)-2,6,6-trimethylbicyclo [3.1.1] heptan-3-yl} borane
Other names : (+)-di-3-pinanylborane, Diisopinocampheylborane, Ipc2BH
Abbreviations Ipc2BH
CAS number [21947-87-5]
SMILES [H]B(C1CC2CC(C1(C))C2(C)(C))C3CC4CC(C3(C))C4(C)(C)
InChI=1/C20H35B/c1-11-15-7-13(19(15,3)4)9-17(11)21-18-10-14-8-16(12(18)2)20(14,5)6/h11-18,21H,7-10H2,1-6H3/t11?,12?,13-,14+,15+,16-,17?,18?
Molecular formula C20H20B
Molar mass 271.18 g mol?1
Appearance colourless solid
References
- Brown, Herbert C.; Yoon, N. M. (1977), Isr. J. Chem. 15: 12–16
- Brown, Herbert C.; Bakthan Singaram (1984). “Improved procedures for the synthesis of diisopinocampheylborane of high optical purity”. J. Org. Chem. 49 (5): 945–947. doi:10.1021/jo00179a041.
- C. F. Lane, J. J. Daniels (1972). “(?)-Isopincampheol”. Org. Synth. 52: 59; Coll. Vol. 6: 719.
- Brown, Herbert C.; Veeraraghavan Ramachandran (1991). “The boron approach to asymmertric synthesis”. Pure & Appl. Chem. 63 (3): 307–316. doi:10.1351/pac199163030307.
- Raj K. Dhar, Kanth V. B. Josyula, Robert Todd “Diisopinocampheylborane” in Encyclopedia of Reagents for Organic Synthesis 2006 John Wiley & Sons, New York. doi:10.1002/047084289X.rd248.pub2. Article Online Posting Date: September 15, 2006
- Michael W. Rathke, Alan A. Millard. (1978). “Boranes in functionalization of olefins to amines: 3-Pinanamine”. Org. Synth. 58: 32; Coll. Vol. 6: 943.
- a b c d e Brown, Herbert C.; George Zweifel (1961). “Hydroboration as a convenient procedure for the asymmetric synthesis of alcohols of high optical purity”. J. Am. Chem. Soc. 83 (2): 486–487. doi:10.1021/ja01463a055.
- Brown, Herbert C.; George Zweifel (1961). “Hydroboration as a convenient procedure for the asymmetric synthesis of alcohols of high optical purity”. J. Am. Chem. Soc. 83 (2): 486–487. doi:10.1021/ja01463a055.
- Brown, Herbert C.; John R. Schwier and Bakthan Singaram (1978). “Simple synthesis of monoisopinocampheylborane of high optical purity”. J. Org. Chem. 43 (32): 4395–4397. doi:10.1021/jo00416a042.
- Ramachandran, V. P.; G-M. Chen, Herbert C. Brown (1996). “Efficient general asymmetric syntheses of 3-substituted 1(3H)-isobenzofuranones in very high enantiomeric excess”. Tetrahedron Lett. 37 (13): 2205–2208. doi:10.1016/0040-4039(96)00260-2.
- Ramachandran, V. P.; S. Pitre, Herbert C. Brown (2002). “Selective Reductions. 59. Effective Intramolecular Asymmetric Reductions of ?-,? and ?-Keto Acids with Diisopinocampheylborane and Intermolecular Asymmetric Reductions of the Corresponding Esters with B-Chlorodiisopinocampheylborane”. J. Org. Chem. 67 (15): 5315–5319. doi:10.1021/jo025594y.
- (?)-ISOPINOCAMPHEOL [Bicyclo[3.1.1]heptan-3-ol, 2,6,6-trimethyl-, [1R-(1?,2?,3?,5?)]-] Ref: Organic Syntheses, Coll. Vol. 6, p.719 (1988); Vol. 52, p.59 (1972)
