메뉴 건너뛰기




Volumn 51, Issue 47, 2012, Pages 11795-11799

Enantioselective synthesis and cross-coupling of tertiary propargylic boronic esters using lithiation-borylation of propargylic carbamates

Author keywords

allenes; boronic esters; cross coupling; lithiation; propargylic alcohols

Indexed keywords

ALLENES; BORONIC ESTERS; CROSS-COUPLINGS; LITHIATION; PROPARGYLIC ALCOHOLS;

EID: 84869479038     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201203198     Document Type: Article
Times cited : (61)

References (79)
  • 4
    • 79959509600 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 5998-6000.
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 5998-6000
  • 5
    • 84870735356 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 7
    • 76349094490 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 1194-1196
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 1194-1196
  • 18
    • 77954850632 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 5142-5145
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 5142-5145
  • 21
    • 84864429921 scopus 로고
    • The terminal alkynyl tBu group was shown to be necessary for the configurational stability of the organolithium at -78 °C; see:, S. Dreller, M. Dyrbusch, D. Hoppe, Synlett 1991, 397-400
    • (1991) Synlett , pp. 397-400
    • Dreller, S.1    Dyrbusch, M.2    Hoppe, D.3
  • 22
    • 79952753398 scopus 로고    scopus 로고
    • configurational instability was overcome using extremely short reaction times in a flow reactor; see:, Y. Tomida, A. Nagaki, J. Yoshida, J. Am. Chem. Soc. 2011, 133, 3744-3747.
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 3744-3747
    • Tomida, Y.1    Nagaki, A.2    Yoshida, J.3
  • 23
    • 84870736783 scopus 로고    scopus 로고
    • [6b] Conversly, the Regioselectivity is Variable and Electrophile-dependent when tBu is in the γ-position. MeOH reacts solely at the γ-position, but TMSCl reacts exclusively at the α-position. Allyl bromide (α:γ=8:1) and MeI (α:γ=1:1.2) give intermediate selectivities
    • [6b] Conversly, the regioselectivity is variable and electrophile-dependent when tBu is in the γ-position. MeOH reacts solely at the γ-position, but TMSCl reacts exclusively at the α-position. Allyl bromide (α:γ=8:1) and MeI (α:γ=1:1.2) give intermediate selectivities.
    • 2CO, and PhNCO React with Lithiated Propargylic Carbamates Exclusively at The γ-position when Ph is at the Terminus
  • 24
    • 84870746183 scopus 로고    scopus 로고
    • Enantiospecificity (e.s.) of a reaction (% e.s.=[(product ee/starting material ee)×100])
    • Enantiospecificity (e.s.) of a reaction (% e.s.=[(product ee/starting material ee)×100])
  • 29
    • 0001572162 scopus 로고
    • a of allylic (53), benzylic (54), and propargylic susbtrates (63); see:, R. Breslow, J. L. Grant, J. Am. Chem. Soc. 1977, 99, 7745-7746.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 7745-7746
    • Breslow, R.1    Grant, J.L.2
  • 35
    • 79952658020 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 2957-2961.
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 2957-2961
  • 44
    • 79955164155 scopus 로고    scopus 로고
    • S. Yu, S. Ma, Chem. Commun. 2011, 47, 5384-5418; for recent examples of the synthesis of enantioenriched trisubstituted allenes, see
    • (2011) Chem. Commun. , vol.47 , pp. 5384-5418
    • Yu, S.1    Ma, S.2
  • 59
    • 70349782336 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 2656-2670
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 2656-2670
  • 62
    • 84870754340 scopus 로고    scopus 로고
    • Some examples of the cross-coupling of tertiary boron species
    • Some examples of the cross-coupling of tertiary boron species
  • 67
    • 84870736434 scopus 로고    scopus 로고
    • For examples of the cross-coupling of α-substituted-unsubstituted allylic boronic acid/esters, see
    • For examples of the cross-coupling of α-substituted-unsubstituted allylic boronic acid/esters, see
  • 79
    • 77949388897 scopus 로고    scopus 로고
    • For the related Pd-catalyzed cross-coupling of a chiral allylic silanoate, which is proposed to occur via a related 6-membered TS, see:, S. C. Denmark, N. S. Werner, J. Am. Chem. Soc. 2010, 132, 3612-3620.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 3612-3620
    • Denmark, S.C.1    Werner, N.S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.