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Volumn , Issue 5, 2009, Pages 0771-0774

New types of o-carborane-based chiral phosphinooxazoline (Cab-PHOX) ligand systems: Synthesis and characterization of chiral Cab-PHOX ligands and their application to asymmetric hydrogenation

(4) Lee, Jong Dae a Thanh, Thien Co b Kim, Tae Jeong b Sang, Ook Kang c

a Chosun University (South Korea)

b Kyungpook National University (South Korea)

c Korea University (South Korea)

Author keywords

Asymmetric hydrogenation; Chiral phosphinooxazoline ligands; Functionalized olefins; O carborane based bidentate ligands; Unfunctionalized olefins

Indexed keywords

EID: 62349091174 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087934 Document Type: Article

Times cited : (7)

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- Synthesis of Cab-PHOX 4 To a stirred solution of Cab PPh2 1 (0.99 g, 3.0 mmol) in 30 mL of THF, which was cooled to -10°C, was added 2.5 M n-BuLi (1.2 mL, 3.0 mmol) via a syringe. The resulting solution was stirred at -10 ° C for 1 h and then added 2-bromooxazoline 3 (0.63 g, 3.3 mmol) through a cannula. The reaction temperature was maintained at -10°C for 1 h. Subsequently the reaction mixture was warmed slowly to r.t. After stirring for an additional 12 h, the solvent was removed under vacuum, and the resulting residue was taken up by fresh column chromatography (RF, 0.6; hexane-benzene, 1:1, Chiral Cab-PHOX 4 was isolated from the reaction solution in 93% yield 1.23 g, 2.8 mmol, HRMS: m/z calcd for [11B 1012C2014N1H 3016O31P, 439.5421; found: 439.5432. Anal. Calcd: C, 54.65; H, 6.88; N, 3.19
- 2).

53
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- Synthesis of Compound 5 A procedure analogous to the preparation of compound 4 was used but instead starting from Cab PCy2 2 (1.02 g, 3.0 mmol, Compound 5 was obtained as pale yellow oil (RF, 0.5; hexane-benzene, 1:1; 1.19 g, 2.64 mmol, 88, HRMS: m/z calcd for [11B 1012C2014N1H 4216O31P, 451.6373; found: 451.6387. Anal. Calcd: C, 53.19; H, 9.37; N, 3.10. Found: C, 53.33; H, 9.34; N, 3.11. IR spectrum (KBr pellet, ν, 2600 (B-H, 1698 (C=N, 2985 (C-H, 2996 cm-1. 1H NMR (300 MHz, CDCl3, δ, 0.87 [d, 3 H, CH(CH3)2, 3J CH-CH3, 6.3 Hz, 0.97 [d, 3 H, CH(CH3) 2, 3JCH-CH3, 6.9 Hz, 1.25 (m, 1 H, P-cyclo-CH, 1.35 m, 2 H, P-cyclo
- 2).

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