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Volumn 21, Issue 18, 2010, Pages 2281-2288

Highly modular P-OP ligands in asymmetric allylic substitution

Author keywords

[No Author keywords available]

Indexed keywords

1 [BIS [4 (TRIFLUOROMETHYL)PHENYL]PHOSPHINO] 3 METHOXY 1 PHENYLPROPAN 2 YL] (1,1' BINAPHTHALEN 2,2' YL)PHOSPHITE; [1 [BIS(4 METHOXYPHENYL)PHOSPHINO] 3 METHOXY 1 PHENYLPROPAN 2 YL] (1,1' BINAPHTHALEN 2,2' YL)PHOSPHITE; BORANE DERIVATIVE; NUCLEOPHILE; PALLADIUM; PHOSPHINE; PHOSPHITE; UNCLASSIFIED DRUG;

EID: 77957110404     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.08.004     Document Type: Article
Times cited : (28)

References (56)
  • 26
    • 77957150052 scopus 로고    scopus 로고
    • 4 for details on our synthetic strategy towards P-OP ligands 1-5
    • 4 for details on our synthetic strategy towards P-OP ligands 1-5.
  • 27
    • 33748941575 scopus 로고    scopus 로고
    • The steric environment at this position has proven to be critical for the catalytic activity of analogous ligands in several asymmetric transformations: C. Jimeno, A. Vidal-Ferran, and M.A. Perics Org. Lett. 8 2006 3895 3898
    • (2006) Org. Lett. , vol.8 , pp. 3895-3898
    • Jimeno, C.1    Vidal-Ferran, A.2    Perics, M.A.3
  • 32
    • 77957157279 scopus 로고    scopus 로고
    • note
    • In conditions identical to those of entry 2 in Table 2, 3-methyl-1-phenylbut-2-en-1-yl acetate was converted to (E)-dimethyl 2-(2-methyl-4-phenylbut-3-en-2-yl)malonate; and cyclohex-2-en-1-yl acetate gave the racemic substitution product.
  • 33
    • 77957113677 scopus 로고    scopus 로고
    • note
    • -, PF 6 - and BAr F -, respectively, indicating a tenuous counteranion effect.
  • 34
    • 77957121545 scopus 로고    scopus 로고
    • note
    • 3-PhCHCHCHPh)(5)]Cl revealed that only two diastereoisomers were present in solution. Heavy signal overlapping did not allow us to unequivocally establish the structure of the two complexes 14 present in solution.
  • 35
    • 77957173833 scopus 로고    scopus 로고
    • note
    • Energetic and geometrical analysis at the full DFT-level of the transition structures for all possible reaction pathways is, even today, extremely time-consuming in systems of such complexity. Calculations on the geometries of the intermediate π-allyl complexes are much quicker and has allowed rationalisation of the stereochemical outcome of asymmetric allylic substitutions
  • 38
    • 77957170774 scopus 로고    scopus 로고
    • note
    • See Experimental for details on the geometry optimisation of complexes 14 at the DFT level. We did not consider the diastereoisomers 14-exo-anti-anti and 14-endo-anti-anti in the calculations, as nucleophilic attack on these substrates by DMM or BZA would lead to (Z)-alkenes 7a or 7d, respectively, neither of which we observed.
  • 39
    • 0141741604 scopus 로고    scopus 로고
    • For a similar Hammett analysis of enantioselectivity in allylic substitutions, see: R.N. Constantine, N. Kim, and R.C. Bunt Org. Lett. 5 2003 2279 2282
    • (2003) Org. Lett. , vol.5 , pp. 2279-2282
    • Constantine, R.N.1    Kim, N.2    Bunt, R.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.