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Volumn 130, Issue 27, 2008, Pages 8669-8676

Amine-directed hydroboration: Scope and limitations

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; BORON COMPOUNDS; IODINE; ORGANIC COMPOUNDS;

EID: 46949108152     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0774663     Document Type: Article
Times cited : (51)

References (53)
  • 22
  • 27
    • 0026686747 scopus 로고
    • For generation of diiodoborane amine complexes and applications for selective hydroboration, see: c
    • For generation of diiodoborane amine complexes and applications for selective hydroboration, see: (c) Reddy, C. K.; Periasamy, M. Tetrahedron 1992, 48, 8329.
    • (1992) Tetrahedron , vol.48 , pp. 8329
    • Reddy, C.K.1    Periasamy, M.2
  • 34
    • 33645173831 scopus 로고
    • The reported chemical shift is 27.2 ppm upfield from trimethyl borate in benzene; our chemical shift value is referenced to boron trifluoride etherate in deuterochloroform
    • (a) Denniston, M. L.; Chiusano, M.; Brown, J.; Martin, D. R. J. Inorg. Nucl. Chem. 1976, 38, 379. The reported chemical shift is "27.2 ppm upfield from trimethyl borate" in benzene; our chemical shift value is referenced to boron trifluoride etherate in deuterochloroform.
    • (1976) J. Inorg. Nucl. Chem , vol.38 , pp. 379
    • Denniston, M.L.1    Chiusano, M.2    Brown, J.3    Martin, D.R.4
  • 36
    • 0034598050 scopus 로고    scopus 로고
    • A value of δ 17.6 ppm is reported for diborane in chloroform by Kanth, J. V. B.; Brown, H. C. Tetrahedron Lett. 2000, 41, 9361.
    • A value of δ 17.6 ppm is reported for diborane in chloroform by Kanth, J. V. B.; Brown, H. C. Tetrahedron Lett. 2000, 41, 9361.
  • 39
    • 0000540071 scopus 로고    scopus 로고
    • Preferred formation of 2-aminoalcohol derivatives has also been observed using N-protected allylic amine substrates that contain electron withdrawing substituents at nitrogen: Fujita, Y.; Irreverre, F.; Witkop, B. J. Am. Chem. Soc. 1964, 86, 1844.
    • (a) Preferred formation of 2-aminoalcohol derivatives has also been observed using N-protected allylic amine substrates that contain electron withdrawing substituents at nitrogen: Fujita, Y.; Irreverre, F.; Witkop, B. J. Am. Chem. Soc. 1964, 86, 1844.
  • 53
    • 46949083736 scopus 로고    scopus 로고
    • Reference 24a describes several reactions of alkenes in the presence of chiral tertiary N-phenylamines. By far the highest enantioselectivities were reported with 2,3-dihydrofuran (0.7 g scale, benzene solution) in the presence of a 1:1 ratio of in situ generated amine boranes i (11.6 ± 2.3% ee for 3-hydroxytetrahydrofuran) or ii (19.2 ± 2.4% ee for 3-hydroxytetrahydrofuran) using a workup consisting of standard base/peroxide oxidative cleavage followed by distillation from the crude product mixture, Chemical Equation Presented) chromatography, redistillation, and ee assay based on optical rotation. In two attempts to repeat the reaction using i (0.107 and 0.056 g scale, we opted not to perform the distillations due to the smaller quantities. The usual uncertainties involving optical rotation were another consideration. Starting with i found αD +19.2, c 3.2, CHCl3; reported αD
    • N2-like displacement of amine by alkene as proposed in ref 24, or to non-covalent interactions involving the chiral amine in the transition state. Except for the experiments using i or ii with 2,3-dihydrofuran in ref 24a, the other examples described in ref 24a, b report ee values in the range of 1-5% ee based on optical rotation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.