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Volumn 49, Issue 41, 2010, Pages 7562-7565

Catalytic asymmetric direct henry reaction of ynals: Short syntheses of (2S,3R)-(+)-xestoaminol C and (-)-codonopsinines

Author keywords

Amino alcohols; Henry reaction; Organocatalysis; Phosphonium salts; Total synthesis

Indexed keywords

AMINO ALCOHOLS; HENRY REACTIONS; ORGANOCATALYSIS; PHOSPHONIUM SALTS; TOTAL SYNTHESIS;

EID: 77957583788     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201004072     Document Type: Article
Times cited : (106)

References (62)
  • 1
    • 0003799267 scopus 로고
    • (Eds.: P.J. Stang F. Diederich), VCH, Weinheim
    • Modern Acetylene Chemistry (Eds.: P.J. Stang, F. Diederich), VCH, Weinheim, 1995.
    • (1995) Modern Acetylene Chemistry
  • 5
    • 8444224706 scopus 로고    scopus 로고
    • For reviews on the catalytic direct alkynylation of aldehydes
    • For reviews on the catalytic direct alkynylation of aldehydes, see: a) P. G. Cozzi, R. Hilgraf, N. Zimmermann, Eur. J. Org. Chem. 2004, 4095-4105;
    • (2004) Eur. J. Org. Chem. , pp. 4095-4105
    • Cozzi, P.G.1    Hilgraf, R.2    Zimmermann, N.3
  • 6
    • 0242635970 scopus 로고    scopus 로고
    • b) L. Pu, Tetrahedron 2003, 59, 9873-9886;
    • (2003) Tetrahedron , vol.59 , pp. 9873-9886
    • Pu, L.1
  • 9
    • 37049085863 scopus 로고
    • For the catalytic asymmetric addition of a nucleophile to ynals to give optically active propargylic alcohols, see: Dialkylzinc
    • For the catalytic asymmetric addition of a nucleophile to ynals to give optically active propargylic alcohols, see: Dialkylzinc a) S. Niwa, K. Soai, J. Chem. Soc. Perkin Trans. 1 1990, 937-943;
    • (1990) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 937-943
    • Niwa, S.1    Soai, K.2
  • 15
    • 0001339893 scopus 로고    scopus 로고
    • [2+2] cycloaddition with ketene
    • [2+2] cycloaddition with ketene g) S. G. Nelson, Z. Wan, Org. Lett. 2000, 2, 1883-1886;
    • (2000) Org. Lett. , vol.2 , pp. 1883-1886
    • Nelson, S.G.1    Wan, Z.2
  • 18
    • 0034638686 scopus 로고    scopus 로고
    • For the enantioselective allylation of ynals with a stoichiometric chiral reagent
    • For the enantioselective allylation of ynals with a stoichiometric chiral reagent, see: S. BouzBouz, F. Pradaux, J. Cossy, C. Ferroud, A. Falguières, Tetrahedron Lett. 2000, 41, 8877-8880.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 8877-8880
    • Bouzbouz, S.1
  • 19
    • 33846593979 scopus 로고    scopus 로고
    • For reviews on the catalytic asymmetric Henry reaction
    • For reviews on the catalytic asymmetric Henry reaction, see: a) J. Boruwa, N. Gogoi, P. P. Saikia, N. C. Barua, Tetrahedron: Asymmetry 2006, 17, 3315-3326;
    • (2006) Tetrahedron: Asymmetry , vol.17 , pp. 3315-3326
    • Boruwa, J.1    Gogoi, N.2    Saikia, P.P.3    Barua, N.C.4
  • 21
    • 84945959007 scopus 로고
    • The first reported catalytic asymmetric direct Henry reaction used a heterobimetallic catalyst
    • The first reported catalytic asymmetric direct Henry reaction used a heterobimetallic catalyst: H. Sasai, T. Suzuki, S. Arai, T. Arai, M. Shibasaki, J. Am. Chem. Soc. 1992, 114, 4418-4420.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 4418-4420
    • Sasai, H.1    Suzuki, T.2    Arai, S.3    Arai, T.4    Shibasaki, M.5
  • 22
    • 36849070344 scopus 로고    scopus 로고
    • The catalytic asymmetric Henry reaction of trifluoromethyl alkynyl ketone has been reported
    • The catalytic asymmetric Henry reaction of trifluoromethyl alkynyl ketone has been reported: a) F. Tur, J. M. Saá, Org. Lett. 2007, 9, 5079-5082;
    • (2007) Org. Lett. , vol.9 , pp. 5079-5082
    • Tur, F.1
  • 25
    • 77957569399 scopus 로고    scopus 로고
    • For anti-selective and enantioselective Henry reactions, see: a) Ref. [10]
    • For anti-selective and enantioselective Henry reactions, see: a) Ref. [10];
  • 28
    • 45549083087 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 3230-3233;
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 3230-3233
  • 33
    • 0037466989 scopus 로고    scopus 로고
    • for the use of silyl nitronate
    • for the use of silyl nitronate, see: h) T. Ooi, K. Doda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 2054-2055;
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 2054-2055
    • Ooi, T.1    Doda, K.2    Maruoka, K.3
  • 35
    • 33746265821 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 3454-3456;
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 3454-3456
  • 39
    • 0001411292 scopus 로고
    • a = 13.55 in water) is more acidic than ethanol (15.9) and allyl alcohol (15.5)
    • a = 13.55 in water) is more acidic than ethanol (15.9) and allyl alcohol (15.5): P. Ballinger, F. A. Long, J. Am. Chem. Soc. 1960, 82, 795-798.
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 795-798
    • Ballinger, P.1    Long, F.A.2
  • 40
    • 77957589960 scopus 로고    scopus 로고
    • note
    • 31P NMR analysis of a mixture of 3-phenylprop-2-yn-1-ol and the iminophosphorane only showed a sharp singlet at δ = 46.1 ppm without the formation of phosphonium alkoxide.
  • 41
    • 77957592455 scopus 로고    scopus 로고
    • note
    • 31 P NMR spectrum at -98 °C.
  • 42
    • 77957558993 scopus 로고    scopus 로고
    • 31P NMR experiment with 4-methyl-4-nitro-1- phenylpent-1-yn-3-ol and the iminophosphorane in THF/DMF (5%) gave a sharper signal at δ = 35.8 ppm. However, the precise role of DMF is still unclear at present
    • A similar 31P NMR experiment with 4-methyl-4-nitro-1-phenylpent-1-yn-3-ol and the iminophosphorane in THF/DMF (5%) gave a sharper signal at δ = 35.8 ppm. However, the precise role of DMF is still unclear at present.
  • 53
    • 0030605868 scopus 로고    scopus 로고
    • For the synthesis of codonopsinine
    • For the synthesis of codonopsinine, see: a) H. Yoda, T. Nakajima, K. Takabe, Tetrahedron Lett. 1996, 37, 5531-5534;
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5531-5534
    • Yoda, H.1    Nakajima, T.2    Takabe, K.3
  • 61
    • 33947255644 scopus 로고    scopus 로고
    • and Refs. [20a-d]
    • i) J. S. Reddy, B. V. Rao, J. Org. Chem. 2007, 72, 2224-2227, and Refs. [20a-d].
    • (2007) J. Org. Chem. , vol.72 , pp. 2224-2227
    • Reddy, J.S.1    Rao, B.V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.