메뉴 건너뛰기




Volumn 122, Issue 38, 2000, Pages 9134-9142

Enantioselective Lewis acid catalyzed Michael reactions of alkylidene malonates. Catalysis by C2-symmetric bis(oxazoline) copper(II) complexes in the synthesis of chiral, differentiated glutarate esters

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; COPPER; ESTER; GLUTARIC ACID; MALONIC ACID DERIVATIVE; OXAZOLINE DERIVATIVE; SILANE DERIVATIVE;

EID: 0034721430     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja002246+     Document Type: Article
Times cited : (174)

References (85)
  • 47
    • 0343602739 scopus 로고    scopus 로고
    • See refs 3h and 3j
    • (c) See refs 3h and 3j.
  • 56
    • 0030566793 scopus 로고    scopus 로고
    • Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921. These workers have also investigated Ti-TADDOL as a stoichiometric promoter of this reaction: Bernardi, A.; Karamfilova, K.; Boschin, G.; Scolastico, C. Tetrahedron Lett. 1995, 36, 1363.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 8921
    • Bernardi, A.1    Colombo, G.2    Scolastico, C.3
  • 57
    • 0028896929 scopus 로고
    • Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921. These workers have also investigated Ti-TADDOL as a stoichiometric promoter of this reaction: Bernardi, A.; Karamfilova, K.; Boschin, G.; Scolastico, C. Tetrahedron Lett. 1995, 36, 1363.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 1363
    • Bernardi, A.1    Karamfilova, K.2    Boschin, G.3    Scolastico, C.4
  • 60
    • 0343602735 scopus 로고    scopus 로고
    • See ref 9e
    • (b) See ref 9e.
  • 61
    • 0343602736 scopus 로고    scopus 로고
    • See refs 3c and 5a
    • See refs 3c and 5a.
  • 65
    • 0343167314 scopus 로고    scopus 로고
    • note
    • Addition times varied between 8 and 16 h. Changing the substrate required reoptimization of addition times. Alkylidene malonate 10i proved resilient to this protocol, affording only 55% conversion under the optimized addition time of 16 h. We suggest that the bulk of this substrate is responsible. From this and other data, we concluded that slow addition would prove insufficient as a general solution.
  • 67
    • 0342297785 scopus 로고    scopus 로고
    • note
    • Geometry optimizations were performed at the PM3(tm) level using the Spartan Semiempirical Program 5.0 (Wavefunction Inc., Irvine, CA 92612) on a Silicon Graphics Impact 10000 (195 MHz, 128 M RAM) running IRIX 6.2. Calculations were performed without counterions or solvent using the following parameters: optcycle = 5000, maxcycle = 10000, charge = 2, multiplicity = 2. Calculations converged (energy difference between cycles <0.0005 kcal/mol) in ≤ 4 h CPU time.
  • 69
    • 0343602731 scopus 로고    scopus 로고
    • note
    • This is not suprising considering that this ring needs to accommodate five 120° angles (C-C-O, C-C-C, and C-O-Cu), one 90° angle (square planar Cu), and two long bonds (2.0 Å, Cu-O). Indeed, a molecular mechanics geometry optimization of this ring alone predicts an identical conformation despite the failure of PM3 to do likewise.
  • 73
    • 0343167311 scopus 로고    scopus 로고
    • References 3f and 3h
    • (b) References 3f and 3h.
  • 75
    • 0342732765 scopus 로고    scopus 로고
    • See also refs 3c and 21
    • (b) See also refs 3c and 21.
  • 76
    • 0029836179 scopus 로고    scopus 로고
    • and references therein
    • Centroid distances in documented edge-face complexes span a range from 4.5 to 7 Å; see: Quan, R. W.; Li, Z.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8156 and references therein.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 8156
    • Quan, R.W.1    Li, Z.2    Jacobsen, E.N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.