메뉴 건너뛰기




Volumn 55, Issue 31, 2016, Pages 9065-9069

Enantio- and Diastereoselective 1,2-Additions to α-Ketoesters with Diborylmethane and Substituted 1,1-Diborylalkanes

Author keywords

asymmetric catalysis; boron; copper; enantioselectivity; reaction mechanisms

Indexed keywords

BORON; CATALYSIS; CHELATION; COPPER; PHOSPHORUS COMPOUNDS; REACTION INTERMEDIATES;

EID: 84978741653     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201603465     Document Type: Article
Times cited : (93)

References (70)
  • 2
    • 85043133883 scopus 로고    scopus 로고
    • For recent reviews on catalytic enantioselective additions to ketones, se
    • For recent reviews on catalytic enantioselective additions to ketones, see:
  • 5
    • 85099670845 scopus 로고    scopus 로고
    • For representative examples of catalytic enantioselective additions of sp, -carbon-based nucleophiles to ketones, se
    • 3-carbon-based nucleophiles to ketones, see:
  • 9
    • 5344225888 scopus 로고    scopus 로고
    • Angew. Chem. 2003, 115, 5647–5650;
    • (2003) Angew. Chem. , vol.115 , pp. 5647-5650
  • 12
    • 53549122582 scopus 로고    scopus 로고
    • Angew. Chem. 2007, 119, 7252–7254;
    • (2007) Angew. Chem. , vol.119 , pp. 7252-7254
  • 16
    • 84863680853 scopus 로고    scopus 로고
    • Angew. Chem. 2012, 124, 3218–3221;
    • (2012) Angew. Chem. , vol.124 , pp. 3218-3221
  • 20
    • 84937139885 scopus 로고    scopus 로고
    • for a recent in direct approach to 1,2-hydroxyborons, se
    • T. P. Blaisdell, J. P. Morken, J. Am. Chem. Soc. 2015, 137, 8712–8715; for a recent in direct approach to 1,2-hydroxyborons, see:
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 8712-8715
    • Blaisdell, T.P.1    Morken, J.P.2
  • 24
    • 84977970427 scopus 로고    scopus 로고
    • Angew. Chem. 2015, 127, 14347–14351.
    • (2015) Angew. Chem. , vol.127 , pp. 14347-14351
  • 37
    • 84977944547 scopus 로고    scopus 로고
    • Angew. Chem. 2016, 128, 1520–1523;
    • (2016) Angew. Chem. , vol.128 , pp. 1520-1523
  • 39
    • 85028875848 scopus 로고    scopus 로고
    • Angew. Chem. 2016, 128, 3516–3519;
    • (2016) Angew. Chem. , vol.128 , pp. 3516-3519
  • 45
    • 84978664599 scopus 로고    scopus 로고
    • Angew. Chem. 2016, 128, 4785–4788;
    • (2016) Angew. Chem. , vol.128 , pp. 4785-4788
  • 48
    • 85043134252 scopus 로고    scopus 로고
    • Absolute configuration of the tertiary alcohol 6 a formed with (R)-MonoPhos is R (see the Supporting Information
    • Absolute configuration of the tertiary alcohol 6 a formed with (R)-MonoPhos is R (see the Supporting Information).
  • 49
    • 85043141395 scopus 로고    scopus 로고
    • Reactions run for 48 h at −25 °C did not lead to an increase in yield
    • Reactions run for 48 h at −25 °C did not lead to an increase in yield.
  • 50
    • 85099672438 scopus 로고    scopus 로고
    • Treatment of, 4 a, with 2 equivalents of LiO, t, Bu (no Cu or, L1,) at −10 °C for 2.5 h results in >98 % conversion of, 4 a, and 90 % conversion to, 6, Treatment of, 4 a, with 2 equivalents of LiO, t, Bu, 5 mol % [Cu(NCMe),]PF, 10 mol %, L1, at −10 °C for 2.5 h results in >98 % conversion of, 4 a, but only 70 % to
    • 6, and 10 mol % L1 at −10 °C for 2.5 h results in >98 % conversion of 4 a but only 70 % to 6.
  • 51
    • 33947616718 scopus 로고    scopus 로고
    • For an example of copper(I)-catalyzed transesterification, se
    • For an example of copper(I)-catalyzed transesterification, see: C. Munro-Leighton, S. A. Delp, E. D. Blue, T. B. Gunnoe, Organometallics 2007, 26, 1483–1493.
    • (2007) Organometallics , vol.26 , pp. 1483-1493
    • Munro-Leighton, C.1    Delp, S.A.2    Blue, E.D.3    Gunnoe, T.B.4
  • 52
    • 85043103003 scopus 로고    scopus 로고
    • The decreased e.r. value is likely due to reaction with LiOEt
    • The decreased e.r. value is likely due to reaction with LiOEt.
  • 54
    • 85043133846 scopus 로고    scopus 로고
    • Increasing the equivalents of LiOtBu or decreasing the reaction temperature does not improve conversion into 10 e
    • Increasing the equivalents of LiOtBu or decreasing the reaction temperature does not improve conversion into 10 e.
  • 55
    • 85043133899 scopus 로고    scopus 로고
    • For examples of stereoretentive reactions of organocopper alkyls, se
    • For examples of stereoretentive reactions of organocopper alkyls, see:
  • 61
    • 84935477841 scopus 로고    scopus 로고
    • for stereoinvertive reactions of organocopper alkyls, se
    • Y. Yang, S.-L. Shi, D. Niu, P. Liu, S. L. Buchwald, Science 2015, 349, 62–66; for stereoinvertive reactions of organocopper alkyls, see:
    • (2015) Science , vol.349 , pp. 62-66
    • Yang, Y.1    Shi, S.-L.2    Niu, D.3    Liu, P.4    Buchwald, S.L.5
  • 62
    • 85043138139 scopus 로고    scopus 로고
    • Ref. [16c]
    • Ref. [16c];
  • 64
    • 84945438698 scopus 로고    scopus 로고
    • Angew. Chem. 2015, 127, 5317–5320.
    • (2015) Angew. Chem. , vol.127 , pp. 5317-5320
  • 65
    • 85043130237 scopus 로고    scopus 로고
    • Steric hindrance of the primary and secondary alkyl boronic esters likely inhibits reaction
    • Steric hindrance of the primary and secondary alkyl boronic esters likely inhibits reaction.
  • 67
    • 0038567454 scopus 로고    scopus 로고
    • Angew. Chem. 2003, 115, 1944–1968.
    • (2003) Angew. Chem. , vol.115 , pp. 1944-1968
  • 69
    • 85043142058 scopus 로고    scopus 로고
    • 24 % unreacted benzophenone. The e.r. value was determined by conversion into the known corresponding diol (see the Supporting Information for details)
    • 24 % unreacted benzophenone. The e.r. value was determined by conversion into the known corresponding diol (see the Supporting Information for details).
  • 70
    • 84978689967 scopus 로고    scopus 로고
    • Studies to elucidate the boron enantiotopic group-selectivity during transmetalation are ongoing.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.