메뉴 건너뛰기




Volumn 53, Issue 9, 2010, Pages 1899-1906

Nickel-catalyzed enantioselective hydrovinylation of silyl-protected allylic alcohols: An efficient access to homoallylic alcohols with a chiral quaternary center

Author keywords

asymmetric hydrovinylation; chiral quaternary center; chiral spiro phosphorus ligands; functionalized olefins

Indexed keywords

ALLYLIC ALCOHOL; BIFUNCTIONAL COMPOUNDS; CHIRAL SPIRO PHOSPHORUS LIGANDS; EFFICIENT METHOD; ENANTIOSELECTIVE; FUNCTIONALIZED; HIGH ENANTIOSELECTIVITY; HIGH YIELD; HOMOALLYLIC ALCOHOL; HYDROVINYLATION; NICKEL COMPLEX; PHOSPHORAMIDITE LIGANDS; QUATERNARY CARBON; QUATERNARY CENTERS;

EID: 77957903398     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-010-4036-6     Document Type: Conference Paper
Times cited : (18)

References (28)
  • 2
    • 0041497165 scopus 로고    scopus 로고
    • Asymmetric hydrovinylation: New perspectives through use of modular ligand systems
    • DOI 10.1002/1521-3773(20021018)41: 20<3775::AID-ANIE3775>3.0.CO;2-2
    • L.J. Goossen 2002 Asymmetric hydrovinylation: New perspectives through use of modular ligand systems Angew Chem Int Ed 41 3775 3778 1:CAS:528:DC%2BD38XosF2hurg%3D 10.1002/1521-3773(20021018)41:20<3775::AID- ANIE3775>3.0.CO;2-2 (Pubitemid 35282430)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.20 , pp. 3775-3778
    • Goossen, L.J.1
  • 3
    • 0041378064 scopus 로고    scopus 로고
    • Asymmetric hydrovinylation reaction
    • 1:CAS:528:DC%2BD3sXksVChsr8%3D 10.1021/cr020040g
    • T.V. RajanBabu 2003 Asymmetric hydrovinylation reaction Chem Rev 103 2845 2860 1:CAS:528:DC%2BD3sXksVChsr8%3D 10.1021/cr020040g
    • (2003) Chem Rev , vol.103 , pp. 2845-2860
    • Rajanbabu, T.V.1
  • 4
    • 0003178361 scopus 로고
    • DOS 3 618 169, priority 30.05.1986
    • G. Wilke J. Monkiewicz 1988 DOS 3 618 169, priority 30.05.1986 Chem. Abstr. 109 6735
    • (1988) Chem. Abstr. , vol.109 , pp. 6735
    • Wilke, G.1    Monkiewicz, J.2
  • 5
    • 0037028566 scopus 로고    scopus 로고
    • Tunable ligands for asymmetric catalysis: Readily available carbohydrate-derived diarylphosphinites induce high selectivity in the hydrovinylation of styrene derivatives
    • DOI 10.1021/ja0172013
    • H. Park T.V. RajanBabu 2002 Tunable ligands for asymmetric catalysis: Readily available carbohydrate-derived diarylphosphinites induce high selectivity in the hydrovinylation of styrene derivatives J Am Chem Soc 124 734 735 1:CAS:528:DC%2BD3MXptVOmurw%3D 10.1021/ja0172013 (Pubitemid 34112766)
    • (2002) Journal of the American Chemical Society , vol.124 , Issue.5 , pp. 734-735
    • Park, H.1    RajanBabu, T.V.2
  • 6
    • 0037028545 scopus 로고    scopus 로고
    • Highly enantioselective nickel-catalyzed hydrovinylation with chiral phosphoramidite ligands
    • DOI 10.1021/ja012099v
    • G. Franciò F. Faraone W. Leitner 2002 Highly enantioselective nickelcatalyzed hydrovinylation with chiral phosphoramidite ligands J Am Chem Soc 124 736 737 10.1021/ja012099v (Pubitemid 34112767)
    • (2002) Journal of the American Chemical Society , vol.124 , Issue.5 , pp. 736-737
    • Francio, G.1    Faraone, F.2    Leitner, W.3
  • 7
    • 2442547591 scopus 로고    scopus 로고
    • Fine-tuning monophosphine ligands for enhanced enantioselectivity. Influence of chiral hemilabile pendant groups
    • DOI 10.1021/ol0495063
    • A. Zhang T.V. RajanBabu 2004 Fine-tuning monophosphine ligands for enhanced enantioselectivity. Influence of chiral hemilabile pendant groups Org Lett 6 1515 1517 1:CAS:528:DC%2BD2cXis1Whtbg%3D 10.1021/ol0495063 (Pubitemid 38626343)
    • (2004) Organic Letters , vol.6 , Issue.9 , pp. 1515-1517
    • Zhang, A.1    RajanBabu, T.V.2
  • 8
    • 44449114350 scopus 로고    scopus 로고
    • Efficient, selective, and green: Catalyst tuning for highly enantioselective reactions of ethylene
    • 1:CAS:528:DC%2BD1cXjsVGnsr8%3D 10.1021/ol800395m
    • C.R. Smith T.V. RajanBabu 2008 Efficient, selective, and green: Catalyst tuning for highly enantioselective reactions of ethylene Org Lett 10 1657 1659 1:CAS:528:DC%2BD1cXjsVGnsr8%3D 10.1021/ol800395m
    • (2008) Org Lett , vol.10 , pp. 1657-1659
    • Smith, C.R.1    Rajanbabu, T.V.2
  • 9
    • 33644952259 scopus 로고    scopus 로고
    • Highly enantioselective hydrovinylation of α-alkyl vinylarenes. An approach to the construction of all-carbon quaternary stereocenters
    • 1:CAS:528:DC%2BD28Xht1eqt70%3D 10.1021/ja057654y
    • W.-J. Shi Q. Zhang J.-H. Xie S.-F. Zhu G.-H. Hou Q.-L. Zhou 2006 Highly enantioselective hydrovinylation of α-alkyl vinylarenes. An approach to the construction of all-carbon quaternary stereocenters J Am Chem Soc 128 2780 2781 1:CAS:528:DC%2BD28Xht1eqt70%3D 10.1021/ja057654y
    • (2006) J Am Chem Soc , vol.128 , pp. 2780-2781
    • Shi, W.-J.1    Zhang, Q.2    Xie, J.-H.3    Zhu, S.-F.4    Hou, G.-H.5    Zhou, Q.-L.6
  • 10
    • 33646540104 scopus 로고    scopus 로고
    • All-carbon quaternary centers via catalytic asymmetric hydrovinylation. New approaches to the exocyclic side chain stereochemistry problem
    • DOI 10.1021/ja060999b
    • A. Zhang T.V. RajanBabu 2006 All-carbon quaternary centers via catalytic asymmetric hydrovinylation. New approaches to the exocyclic side chain stereochemistry problem J Am Chem Soc 128 5620 5621 1:CAS:528: DC%2BD28XjtleqsLc%3D 10.1021/ja060999b (Pubitemid 43724349)
    • (2006) Journal of the American Chemical Society , vol.128 , Issue.17 , pp. 5620-5621
    • Zhang, A.1    RajanBabu, T.V.2
  • 11
    • 0344927928 scopus 로고    scopus 로고
    • Hydrovinylation of Norbornene. Ligand-Dependent Selectivity and Asymmetric Variations
    • DOI 10.1021/ol0356284
    • R. Kumareswaran M. Nandi T.V. RajanBabu 2003 Hydrovinylation of norbornene. Ligand-dependent selectivity and asymmetric variations Org Lett 5 4345 4348 1:CAS:528:DC%2BD3sXot1Ojt70%3D 10.1021/ol0356284 (Pubitemid 37490625)
    • (2003) Organic Letters , vol.5 , Issue.23 , pp. 4345-4348
    • Kumareswaran, R.1    Nandi, M.2    RajanBabu, T.V.3
  • 12
    • 30744472967 scopus 로고    scopus 로고
    • Hydrovinylation of 1,3-dienes: A new protocol, an asymmetric variation, and a potential solution to the exocyclic side chain stereochemistry problem
    • DOI 10.1021/ja0561338
    • A. Zhang T.V. RajanBabu 2006 Hydrovinylation of 1,3-dienes: A new protocol, an asymmetric variation, and a potential solution to the exocyclic side chain stereochemistry problem J Am Chem Soc 128 54 55 1:CAS:528: DC%2BD2MXht1yrsLjO 10.1021/ja0561338 (Pubitemid 43100845)
    • (2006) Journal of the American Chemical Society , vol.128 , Issue.1 , pp. 54-55
    • Zhang, A.1    RajanBabu, T.V.2
  • 14
    • 53849096350 scopus 로고    scopus 로고
    • Nickel-catalyzed highly selective hydrovinylation of α-ketals of vinylarenes
    • 1:CAS:528:DC%2BD1cXos1KjtL4%3D 10.1002/adsc.200800158
    • Q. Zhang S.-F. Zhu X.-C. Qiao L.-X. Wang Q.-L. Zhou 2008 Nickel-catalyzed highly selective hydrovinylation of α-ketals of vinylarenes Adv Synth Catal 350 1507 1510 1:CAS:528:DC%2BD1cXos1KjtL4%3D 10.1002/adsc.200800158
    • (2008) Adv Synth Catal , vol.350 , pp. 1507-1510
    • Zhang, Q.1    Zhu, S.-F.2    Qiao, X.-C.3    Wang, L.-X.4    Zhou, Q.-L.5
  • 15
    • 44649197822 scopus 로고    scopus 로고
    • Chiral diphosphine and monodentate phosphorous ligands on a spiro scaffold for transition-metal-catalyzed asymmetric reactions
    • 1:CAS:528:DC%2BD1cXis1Ght7c%3D 10.1021/ar700137z
    • J.-H. Xie Q.-L. Zhou 2008 Chiral diphosphine and monodentate phosphorous ligands on a spiro scaffold for transition-metal-catalyzed asymmetric reactions Acc Chem Res 41 581 593 1:CAS:528:DC%2BD1cXis1Ght7c%3D 10.1021/ar700137z
    • (2008) Acc Chem Res , vol.41 , pp. 581-593
    • Xie, J.-H.1    Zhou, Q.-L.2
  • 16
    • 33947477381 scopus 로고
    • Tropine dl-α-methyltropate (methyltropine) and its optical antipodes
    • 1:CAS:528:DyaF3MXhvVSltQ%3D%3D 10.1021/jo01075a624
    • G. Melone A. Vecchi G. Pagani E. Testa 1960 Tropine dl-α- methyltropate (methyltropine) and its optical antipodes J Org Chem 25 859 861 1:CAS:528:DyaF3MXhvVSltQ%3D%3D 10.1021/jo01075a624
    • (1960) J Org Chem , vol.25 , pp. 859-861
    • Melone, G.1    Vecchi, A.2    Pagani, G.3    Testa, E.4
  • 18
    • 0000393822 scopus 로고
    • Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Highly lipophilic stable anionic agent for solvent-extraction cations
    • 1:CAS:528:DyaL2cXlslymtb4%3D 10.1246/bcsj.57.2600
    • H. Nishida N. Takada M. Yoshimura T. Sonoda H. Kobayashi 1984 Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Highly lipophilic stable anionic agent for solvent-extraction cations Bull Chem Soc Jpn 57 2600 2604 1:CAS:528:DyaL2cXlslymtb4%3D 10.1246/bcsj.57.2600
    • (1984) Bull Chem Soc Jpn , vol.57 , pp. 2600-2604
    • Nishida, H.1    Takada, N.2    Yoshimura, M.3    Sonoda, T.4    Kobayashi, H.5
  • 19
    • 0011438965 scopus 로고
    • +: A convenient reagent for generation and stabilization of cationic, highly electrophilic organometallic complexes
    • 1:CAS:528:DyaK3sXhtVajs7Y%3D 10.1021/om00059a071
    • +: A convenient reagent for generation and stabilization of cationic, highly electrophilic organometallic complexes Organometallics 11 3920 3922 1:CAS:528:DyaK3sXhtVajs7Y%3D 10.1021/om00059a071
    • (1992) Organometallics , vol.11 , pp. 3920-3922
    • Brookhart, M.1    Grant, B.2    Volpe, Jr.A.F.3
  • 20
    • 0037458797 scopus 로고    scopus 로고
    • Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to enones using chiral spiro phosphoramidites as ligands
    • DOI 10.1021/jo026611m
    • H. Zhou W.-H. Wang Y. Fu J.-H. Xie W.-J. Shi L.-X. Wang Q.-L. Zhou 2003 Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to enones using chiral spiro phosphoramidites as ligands J Org Chem 68 1582 1584 1:CAS:528:DC%2BD3sXisVylsA%3D%3D 10.1021/jo026611m (Pubitemid 36232529)
    • (2003) Journal of Organic Chemistry , vol.68 , Issue.4 , pp. 1582-1584
    • Zhou, H.1    Wang, W.-H.2    Fu, Y.3    Xie, J.-H.4    Shi, W.-J.5    Wang, L.-X.6    Zhou, Q.-L.7
  • 21
    • 0344740021 scopus 로고    scopus 로고
    • Highly regioselective asymmetric copper-catalyzed allylic alkylation with dialkylzincs using monodentate chiral spiro phosphoramidite and phosphite ligands
    • DOI 10.1016/j.tetasy.2003.09.028
    • W.-J. Shi L.-X. Wang Y. Fu S.-F. Zhu Q.-L. Zhou 2003 Highly regioselective asymmetric copper-catalyzed allylic alkylation with dialkylzinc using monodentate chiral spiro phosphoramidite and phosphite ligands Tetrahedron: Asymmetry 14 3867 3872 1:CAS:528:DC%2BD3sXpsVKktLs%3D 10.1016/j.tetasy.2003.09.028 (Pubitemid 37504992)
    • (2003) Tetrahedron Asymmetry , vol.14 , Issue.24 , pp. 3867-3872
    • Shi, W.-J.1    Wang, L.-X.2    Fu, Y.3    Zhu, S.-F.4    Zhou, Q.-L.5
  • 22
    • 33847652798 scopus 로고    scopus 로고
    • Asymmetric reductive coupling of dienes and aldehydes catalyzed by nickel complexes of spiro phosphoramidites: Highly enantioselective synthesis of chiral bishomoallylic alcohols
    • DOI 10.1021/ja0693183
    • Y. Yang S.-F. Zhu H.-F. Duan C.-Y. Zhou L.-X. Wang Q.-L. Zhou 2007 Asymmetric reductive coupling of dienes and aldehydes catalyzed by nickel complexes of spiro phosphoramidites: Highly enantioselective synthesis of chiral bishomoallylic alcohols J Am Chem Soc 129 2248 2249 1:CAS:528: DC%2BD2sXht1Kisb8%3D 10.1021/ja0693183 (Pubitemid 46362536)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.8 , pp. 2248-2249
    • Yang, Y.1    Zhu, S.-F.2    Duan, H.-F.3    Zhou, C.-Y.4    Wang, L.-X.5    Zhou, Q.-L.6
  • 23
    • 0002819366 scopus 로고
    • Reactifs de grignard vinyliques γ fonctionnels: I. Reactivite des organomagnesiens vis-a-vis d'alcools α acetyleniques en presence d'halogenures cuivreux
    • 1:CAS:528:DyaE1MXitVensLs%3D 10.1016/S0022-328X(00)91989-2
    • J.G. Duboudin B. Jousseaume A. Saux 1979 Reactifs de grignard vinyliques γ fonctionnels: I. Reactivite des organomagnesiens vis-a-vis d'alcools α acetyleniques en presence d'halogenures cuivreux J Organomet Chem 168 1 11 1:CAS:528:DyaE1MXitVensLs%3D 10.1016/S0022-328X(00)91989-2
    • (1979) J Organomet Chem , vol.168 , pp. 1-11
    • Duboudin, J.G.1    Jousseaume, B.2    Saux, A.3
  • 24
    • 14644404952 scopus 로고    scopus 로고
    • 2-Arylallyl as a new protecting group for amines, amides and alcohols
    • Barluenga J, Fañanás FJ, Sanz R, Marcos C, Ignacio J M. 2-Arylallyl as a new protecting group for amines, amides and alcohols. Chem Commun, 2005, 933-935
    • (2005) Chem Commun , pp. 933-935
    • Barluenga, J.1
  • 25
    • 0001619466 scopus 로고
    • Palladium catalyzed coupling of organostannanes with vinyl epoxides
    • 1:CAS:528:DyaL1MXmtFCitLs%3D 10.1016/0040-4020(89)80010-9
    • D.R. Tueting A.M. Echavarren J.K. Stille 1989 Palladium catalyzed coupling of organostannanes with vinyl epoxides Tetrahedron 45 979 992 1:CAS:528:DyaL1MXmtFCitLs%3D 10.1016/0040-4020(89)80010-9
    • (1989) Tetrahedron , vol.45 , pp. 979-992
    • Tueting, D.R.1    Echavarren, A.M.2    Stille, J.K.3
  • 26
    • 0027406122 scopus 로고
    • Asymmetric construction of quaternary carbons from chiral malonates: Total syntheses of (+)-epilaurene and (-)-isolaurene
    • DOI 10.1016/S0957-4166(00)86009-7
    • A. Fadel J.L. Canet J. Salaün 1993 Asymmetric construction of quaternary carbons from chiral malonates: total synthesis of (+)-epilaurene and (-)-isolaurene Tetrahedron: Asymmetry 4 27 30 1:CAS:528:DyaK3sXitFegsrg%3D 10.1016/S0957-4166(00)86009-7 (Pubitemid 23046285)
    • (1993) Tetrahedron Asymmetry , vol.4 , Issue.1 , pp. 27-30
    • Fadel, A.1    Canet, J.-L.2    Salaun, J.3
  • 27
    • 0033605531 scopus 로고    scopus 로고
    • Total synthesis of (-)-sporochnol A, the fish deterrent, from a chiral malonate
    • DOI 10.1016/S0957-4166(99)00086-5, PII S0957416699000865
    • A. Fadel L. Vandromme 1999 Total synthesis of (-)-sporochnol A, the fish deterrent from a chiral malonate Tetrahedron: Asymmetry 10 1153 1162 1:CAS:528:DyaK1MXjt1Orsbo%3D 10.1016/S0957-4166(99)00086-5 (Pubitemid 29223140)
    • (1999) Tetrahedron Asymmetry , vol.10 , Issue.6 , pp. 1153-1162
    • Fadel, A.1    Vandromme, L.2
  • 28
    • 33847660868 scopus 로고    scopus 로고
    • Easy access to esters with a benzylic quaternary carbon center from diallyl malonates by palladium-catalyzed decarboxylative allylation
    • DOI 10.1021/jo0621569
    • D. Imao A. Itoi A. Yamazaki M. Shirakura R. Ohtoshi K. Ogata Y. Ohmori T. Ohta Y. Ito 2007 Easy access to esters with a benzylic quaternary carbon center from diallyl malonates by palladium-catalyzed decarboxylative allylation J Org Chem 72 1652 1658 1:CAS:528:DC%2BD2sXht1Kis7w%3D 10.1021/jo0621569 (Pubitemid 46355462)
    • (2007) Journal of Organic Chemistry , vol.72 , Issue.5 , pp. 1652-1658
    • Imao, D.1    Itoi, A.2    Yamazaki, A.3    Shirakura, M.4    Ohtoshi, R.5    Ogata, K.6    Ohmori, Y.7    Ohta, T.8    Ito, Y.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.