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Volumn 133, Issue 28, 2011, Pages 10728-10731

Bulky, optically active P-stereogenic phosphine-boranes from pure H-menthylphosphinates

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOMERIC EXCESS; ENANTIOPURE; OPTICALLY ACTIVE; PHOSPHA-PALLADACYCLE;

EID: 79960273999     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2034816     Document Type: Article
Times cited : (120)

References (85)
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    • Reference 1d.
    • Reference 1d.
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    • Recently, synthesis of P-stereogenic aminophosphines with tert -butyl group was reported.
    • Recently, synthesis of P-stereogenic aminophosphines with tert -butyl group was reported. León, T.; Riera, A.; Verdaguer, X. J. Am. Chem. Soc. 2011, 133, 5740-5743
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 5740-5743
    • León, T.1    Riera, A.2    Verdaguer, X.3
  • 44
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    • For examples of a dynamic thermodynamic resolution using phosphine-borane in alkylation reactions see
    • For examples of a dynamic thermodynamic resolution using phosphine-borane in alkylation reactions see: Wolfe, B.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 5116-5117
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5116-5117
    • Wolfe, B.1    Livinghouse, T.2
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    • For a similar example see
    • For a similar example see: Xu, Q.; Zhao, C. Q.; Han, L. B. J. Am. Chem. Soc. 2008, 130, 12648-12655
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 12648-12655
    • Xu, Q.1    Zhao, C.Q.2    Han, L.B.3
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    • Reference 12a.
    • Reference 12a.
  • 60
    • 79960276042 scopus 로고    scopus 로고
    • Reference 12c.
    • Reference 12c.
  • 61
    • 20344364653 scopus 로고    scopus 로고
    • 31P NMR spectrum of two multiplets at 124.1 and 139.5 ppm was characteristic of 6 and 7, respectively.
    • 31P NMR spectrum of two multiplets at 124.1 and 139.5 ppm was characteristic of 6 and 7, respectively. Stankevic, M.; Pietrusiewicz, K. M. Synthesis 2005, 1279-1290
    • (2005) Synthesis , pp. 1279-1290
    • Stankevic, M.1    Pietrusiewicz, K.M.2
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    • 33845278221 scopus 로고
    • The reduction reaction is known to proceed with total inversion of configuration.
    • The reduction reaction is known to proceed with total inversion of configuration. Skrzypczynski, Z.; Michalski, J. J. Org. Chem. 1988, 53, 4549-4551
    • (1988) J. Org. Chem. , vol.53 , pp. 4549-4551
    • Skrzypczynski, Z.1    Michalski, J.2
  • 63
    • 79960244639 scopus 로고    scopus 로고
    • 31P NMR
    • 31P NMR
  • 64
    • 79960241442 scopus 로고    scopus 로고
    • See ref 9b.
    • See ref 9b.
  • 67
    • 79960283336 scopus 로고    scopus 로고
    • P)- 9i confirms our hypothesis for absolute configuration at the phosphorus atom of 1b.
    • P)- 9i confirms our hypothesis for absolute configuration at the phosphorus atom of 1b.
  • 68
    • 79960239277 scopus 로고    scopus 로고
    • Reduction step occurs with total inversion of configuration, whereas the mesylation and alkylation steps proceed with full retention of configurations.
    • Reduction step occurs with total inversion of configuration, whereas the mesylation and alkylation steps proceed with full retention of configurations.
  • 69
    • 79960225187 scopus 로고    scopus 로고
    • Bidentate P,N ligands see: Reference 1d pp.
    • Bidentate P,N ligands see: Reference 1d pp 549-632.
  • 71
    • 79952684475 scopus 로고    scopus 로고
    • For a recent review concerning the applications of P,N ligands in transition metal-catalyzed enantioselective hydrogenation of enamines and imines see
    • For a recent review concerning the applications of P,N ligands in transition metal-catalyzed enantioselective hydrogenation of enamines and imines see: Xie, J.-H.; Fhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713-1760
    • (2011) Chem. Rev. , vol.111 , pp. 1713-1760
    • Xie, J.-H.1    Fhu, S.-F.2    Zhou, Q.-L.3
  • 72
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    • The erosion of the enantioselectivity is probably attributed to the racemization of the phosphido-borane anion see
    • The erosion of the enantioselectivity is probably attributed to the racemization of the phosphido-borane anion see: Imamoto, T.; Oshiki, T.; Onozawa, T.; Matsuo, M.; Hikosaka, T.; Yanagawa, M. Heteroat. Chem. 1992, 3, 563-575
    • (1992) Heteroat. Chem. , vol.3 , pp. 563-575
    • Imamoto, T.1    Oshiki, T.2    Onozawa, T.3    Matsuo, M.4    Hikosaka, T.5    Yanagawa, M.6
  • 73
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    • See ref 19b.
    • See ref 19b.
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    • Comparison of the enantiomeric excesses of 9h before and after the DABCO deprotection-reprotection sequence confirmed P-stereochemical integrity.
    • Comparison of the enantiomeric excesses of 9h before and after the DABCO deprotection-reprotection sequence confirmed P-stereochemical integrity.
  • 79
    • 79960226865 scopus 로고    scopus 로고
    • In solution, the dimeric complex exists as an equilibrium mixture of the two possible cis - and trans -diastereomers (see Figure 1)
    • In solution, the dimeric complex exists as an equilibrium mixture of the two possible cis-and trans -diastereomers (see Figure 1)
  • 84
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    • See ref 30.
    • See ref 30.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.