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Volumn 46, Issue 45, 2007, Pages 8636-8639

Synthesis and enantioselectivity of P-chiral phosphine ligands with alkynyl groups

Author keywords

Asymmetric catalysis; Boranes; Hydrogenation; Nucleophilic substitution; Phosphane ligands

Indexed keywords

BORON COMPOUNDS; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; NUCLEOPHILES; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 36549005121     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200702513     Document Type: Article
Times cited : (112)

References (49)
  • 7
    • 0001912409 scopus 로고
    • Eds, J. D. Morrison, J. W. Scott, Academic Press, New York, chap. 3, p
    • g) D. Valentine, Jr. in Asymmetric Synthesis, Vol. 4 (Eds.: J. D. Morrison, J. W. Scott), Academic Press, New York, 1984, chap. 3, p. 263;
    • (1984) Asymmetric Synthesis , vol.4 , pp. 263
    • Valentine Jr., D.1
  • 8
    • 0042373624 scopus 로고
    • Ed, R. Engel, Marcel Dekker, New York, chap. 1, pp
    • h) T. Imamoto in Handbook of Organophosphorus Chemistry (Ed.: R. Engel), Marcel Dekker, New York, 1992, chap. 1, pp. 1-52.
    • (1992) Handbook of Organophosphorus Chemistry , pp. 1-52
    • Imamoto, T.1
  • 9
    • 1642361752 scopus 로고    scopus 로고
    • For representative reviews, see: a
    • For representative reviews, see: a) P.-H. Leung, Acc. Chem. Res. 2004, 37, 169-177;
    • (2004) Acc. Chem. Res , vol.37 , pp. 169-177
    • Leung, P.-H.1
  • 19
    • 24144436977 scopus 로고    scopus 로고
    • T. Imamoto, K. Sugita, K. Yoshida, J. Am. Chem. Soc. 2005, 127, 11934-11935 (tBu-QuinoxP* = 2,3-bis(tert-butylmethylphosphanyl)quinoxaline).
    • f) T. Imamoto, K. Sugita, K. Yoshida, J. Am. Chem. Soc. 2005, 127, 11934-11935 (tBu-QuinoxP* = 2,3-bis(tert-butylmethylphosphanyl)quinoxaline).
  • 27
    • 36549084571 scopus 로고    scopus 로고
    • The stereochemical course of the reaction was confirmed on the basis of the absolute configuration of the substitution product 3a. The absolute configuration of compound 6a, which is derived from 3a, was determined to be S,S by single-crystal X-ray analysis. Hence, 3a has the S configuration, which indicates that the substitution reaction occurred with inversion of configuration see the Supporting Information
    • The stereochemical course of the reaction was confirmed on the basis of the absolute configuration of the substitution product 3a. The absolute configuration of compound 6a, which is derived from 3a, was determined to be S,S by single-crystal X-ray analysis. Hence, 3a has the S configuration, which indicates that the substitution reaction occurred with inversion of configuration (see the Supporting Information).
  • 29
    • 36549038591 scopus 로고    scopus 로고
    • The chlorinated compound (R)-(tert-butyl-(chloro)methylphosphanyl) borane was prepared by treating 1 with nBuLi and hexachloroethane. It exists as a stable crystalline solid and hardly reacted at all with benzylmagnesium chloride at room temperature.
    • The chlorinated compound (R)-(tert-butyl-(chloro)methylphosphanyl) borane was prepared by treating 1 with nBuLi and hexachloroethane. It exists as a stable crystalline solid and hardly reacted at all with benzylmagnesium chloride at room temperature.
  • 30
    • 33845959705 scopus 로고    scopus 로고
    • Gold(I) complexes of triethynylphosphine ligands with bulky substituents at the alkyne termini show unique catalytic activity: A. Ochida, H. Ito, M. Sawamura, J. Am. Chem. Soc. 2006, 128, 16486-16487;
    • Gold(I) complexes of triethynylphosphine ligands with bulky substituents at the alkyne termini show unique catalytic activity: A. Ochida, H. Ito, M. Sawamura, J. Am. Chem. Soc. 2006, 128, 16486-16487;
  • 34
    • 36549039532 scopus 로고    scopus 로고
    • To examine the possibility that the alkynyl group of these ligands could be hydrogenated under the reaction conditions, a 1:1 mixture of 5a and [Rh(nbd)2]BF4 in methanol was stirred under 1 atm of hydrogen pressure at room temperature for 3 h. The 1H NMR spectra of the reaction mixture were very complicated, and we could not clarify whether the alkynyl group was hydrogenated or not. On the other hand, 6a was recovered unchanged after being stirred as a solution in methanol in the presence of 5a/[Rh(nbd)2]BF4 5 mol, under 3 atm of hydrogen pressure at room temperature for 5 h
    • 4 (5 mol%) under 3 atm of hydrogen pressure at room temperature for 5 h.
  • 40
    • 0037243669 scopus 로고    scopus 로고
    • and references therein
    • f) K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196, and references therein.
    • (2003) Chem. Rev , vol.103 , pp. 169-196
    • Fagnou, K.1    Lautens, M.2
  • 41
    • 36549017046 scopus 로고    scopus 로고
    • The catalytic efficiency of the structurally analogous and electron-rich phosphine ligand tBu-BisP* was tested in the reaction of 2-cyclohexenone with phenylboronic acid under the same conditions as those described in Table 2. The reaction at 40°C for 2 h afforded the corresponding 1,4-addition product with 20% ee in 37% yield.
    • The catalytic efficiency of the structurally analogous and electron-rich phosphine ligand tBu-BisP* was tested in the reaction of 2-cyclohexenone with phenylboronic acid under the same conditions as those described in Table 2. The reaction at 40°C for 2 h afforded the corresponding 1,4-addition product with 20% ee in 37% yield.
  • 46
    • 4544377519 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 3944-3947;
    • (2004) Chem. Int. Ed , vol.43 , pp. 3944-3947
    • Angew1
  • 48
    • 34248519239 scopus 로고    scopus 로고
    • Ad-QuinoxP*, 2,3-bis(adamantylmethylphosphanyl) quinoxaline
    • T. Imamoto, A. Kumada, K. Yoshida, Chem. Lett. 2007, 36, 500-501 (Ad-QuinoxP* = 2,3-bis(adamantylmethylphosphanyl) quinoxaline).
    • (2007) Chem. Lett , vol.36 , pp. 500-501
    • Imamoto, T.1    Kumada, A.2    Yoshida, K.3
  • 49
    • 36549055101 scopus 로고    scopus 로고
    • 2(cod)]/tBu-BisP* (2 mol %) at room temperature for 6 h to give (1S,2S)-2-ethyl-1,2-dihydronaphthalen-1-ol in 93% yield with 94% ee.
    • 2(cod)]/tBu-BisP* (2 mol %) at room temperature for 6 h to give (1S,2S)-2-ethyl-1,2-dihydronaphthalen-1-ol in 93% yield with 94% ee.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.