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Volumn 132, Issue 38, 2010, Pages 13191-13193

Stereospecific Suzuki-Miyaura coupling of chiral α-(Acylamino) benzylboronic esters with inversion of configuration

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BROMIDES; ENANTIOMERIC EXCESS; HIGH YIELD; INVERSION OF CONFIGURATION; STEREOSPECIFIC; SUZUKI-MIYAURA COUPLING;

EID: 77957126089     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja106632j     Document Type: Article
Times cited : (227)

References (46)
  • 13
    • 77957145447 scopus 로고    scopus 로고
    • Suzuki-Miyaura coupling of sec-alkylboron compounds other than cyclopropylboron compounds
    • Suzuki-Miyaura coupling of sec-alkylboron compounds other than cyclopropylboron compounds
  • 20
    • 28344434347 scopus 로고    scopus 로고
    • Enantioenriched 1, 5, 7, 9a, and 9d were prepared in 10 mmol scale via Matteson's asymmetric homologation starting from (-)-pinanediol derivative 12 as shown in the scheme below. In;, Ed.; Wiley-VCH: Weinheim,; p
    • Enantioenriched 1, 5, 7, 9a, and 9d were prepared in 10 mmol scale via Matteson's asymmetric homologation starting from (-)-pinanediol derivative 12 as shown in the scheme below. Matteson, D. S. In Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2005; p 305.
    • (2005) Boronic Acids , pp. 305
    • Matteson, D.S.1    Hall, D.G.2
  • 23
    • 77957109456 scopus 로고    scopus 로고
    • 2O, and KF) gave poor results: reaction of 1 with 2a gave 3 in 55% yield with only 6% es
    • 2O, and KF) gave poor results: reaction of 1 with 2a gave 3 in 55% yield with only 6% es.
  • 24
    • 77957124734 scopus 로고    scopus 로고
    • Preliminary screening indicated that protodeborylation of 1 was slower in toluene than in 1,4-dioxane
    • Preliminary screening indicated that protodeborylation of 1 was slower in toluene than in 1,4-dioxane.
  • 25
    • 77957159824 scopus 로고    scopus 로고
    • The term enantiospecificity [% es = (product ee/starting material ee) × 100] has been used to describe the conservation of optical purity over the course of stereospecific reactions
    • The term enantiospecificity [% es = (product ee/starting material ee) × 100] has been used to describe the conservation of optical purity over the course of stereospecific reactions
  • 32
    • 77957151779 scopus 로고    scopus 로고
    • Larger scale reaction of 9a (317 mg, 1.0 mmol) with 2a (205 mg, 1.2 mmol) was also successfully achieved under the optimized conditions to give 10a in 80% yield (225 mg) with 97% es
    • Larger scale reaction of 9a (317 mg, 1.0 mmol) with 2a (205 mg, 1.2 mmol) was also successfully achieved under the optimized conditions to give 10a in 80% yield (225 mg) with 97% es.
  • 33
    • 77957110578 scopus 로고    scopus 로고
    • Water (2 equiv) was used in all reactions according to our previous study (ref 6), in which addition of water was crucial in gaining coupling product in high yields. We eventually found that water had no critical effect on the yield or es in the present coupling system
    • Water (2 equiv) was used in all reactions according to our previous study (ref 6), in which addition of water was crucial in gaining coupling product in high yields. We eventually found that water had no critical effect on the yield or es in the present coupling system.
  • 34
    • 77957154836 scopus 로고    scopus 로고
    • For details, see Supporting Information
    • For details, see Supporting Information.
  • 35
    • 77957137231 scopus 로고    scopus 로고
    • 2. For details, see Supporting Information
    • 2. For details, see Supporting Information.
  • 36
    • 0020826828 scopus 로고
    • The mechanism has been proposed for coupling of chiral benzylic stannanes and silanes, which proceed with full or partial inversion of configuration
    • The mechanism has been proposed for coupling of chiral benzylic stannanes and silanes, which proceed with full or partial inversion of configuration. Labadie, J. W. and Stille, J. K. J. Am. Chem. Soc. 1983, 105, 6129
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 6129
    • Labadie, J.W.1    Stille, J.K.2
  • 38
    • 10044233148 scopus 로고    scopus 로고
    • For related reviews, see: Angew. Chem., Int. Ed. 2004, 43, 4704
    • Kells, K. W. and Chong, J. M. J. Am. Chem. Soc. 2004, 126, 15666 For related reviews, see: Espinet, P. and Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 15666
    • Kells, K.W.1    Chong, J.M.2    Espinet, P.3    Echavarren, A.M.4
  • 41
    • 77957107981 scopus 로고    scopus 로고
    • Conversion of the C-B bond in trialkylboranes with inversion of configuration
    • Conversion of the C-B bond in trialkylboranes with inversion of configuration
  • 44
    • 0000369726 scopus 로고
    • 11B NMR chemical shifts of α-(acylamino)benzylboronic esters (δ 14-16 ppm) indicate intramolecular coordination of the carbonyl groups to the boron atoms
    • 11B NMR chemical shifts of α-(acylamino)benzylboronic esters (δ 14-16 ppm) indicate intramolecular coordination of the carbonyl groups to the boron atoms. Biedrzycki, M., Scouten, W. H., and Biedrzycka, Z. J. Organomet. Chem. 1992, 431, 255
    • (1992) J. Organomet. Chem. , vol.431 , pp. 255
    • Biedrzycki, M.1    Scouten, W.H.2    Biedrzycka, Z.3
  • 45
    • 77957119064 scopus 로고    scopus 로고
    • 3 (1 equiv) in toluene at 110 °C for 6 h were as follows: 1 (86% es), 5 (94% es), and 9a (96% es). On the other hand, we confirmed that no racemization of the coupling products, diarylmethanamines, took place under the coupling conditions reported
    • 3 (1 equiv) in toluene at 110 °C for 6 h were as follows: 1 (86% es), 5 (94% es), and 9a (96% es). On the other hand, we confirmed that no racemization of the coupling products, diarylmethanamines, took place under the coupling conditions reported.
  • 46
    • 77950417415 scopus 로고    scopus 로고
    • Inversion of configuration at the oxidative addition step has been reported in the Suzuki-Miyaura coupling of chiral alkyl triflates with aryl boronic acids
    • Inversion of configuration at the oxidative addition step has been reported in the Suzuki-Miyaura coupling of chiral alkyl triflates with aryl boronic acids. He, A. and Falck, J. R. J. Am. Chem. Soc. 2010, 132, 2524
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 2524
    • He, A.1    Falck, J.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.