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Volumn 39, Issue 20, 2009, Pages 3710-3721

Synthesis of chiral sulfamide-amine alcohol ligands for enantioselective alkylation of aldehydes

Author keywords

Amine alcohols; Asymmetric addition; Diethylzinc; Enantioselectivities

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; AMINOALCOHOL; DIETHYLZINC; LEWIS ACID; SULFAMIDE AMINE ALCOHOL DERIVATIVE; SULFAMIDE DERIVATIVE; TITANIUM; UNCLASSIFIED DRUG;

EID: 70349219890     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902806265     Document Type: Article
Times cited : (10)

References (27)
  • 1
    • 0001158063 scopus 로고    scopus 로고
    • E.N. Jacobsen, A. Pfaltz, H. Yamamoto, (Eds.); Springer: Berlin
    • Soai, K.; Shibata, T. In Comprehensive Asymmetric Catalysis; E.N. Jacobsen, A. Pfaltz, H. Yamamoto, (Eds.); Springer: Berlin, 1999; pp. 911-922
    • (1999) In Comprehensive Asymmetric Catalysis , pp. 911-922
    • Soai, K.1    Shibata, T.2
  • 5
    • 0035263817 scopus 로고    scopus 로고
    • Catalytic asymmetric organozinc additions to carbonyl compounds
    • Pu, L.; Yu, H. B. Catalytic asymmetric organozinc additions to carbonyl compounds. Chem. Rev. 2001, 10, 757.
    • (2001) Chem. Rev. , vol.10 , pp. 757
    • Pu, L.1    Yu, H.B.2
  • 6
    • 4244117250 scopus 로고
    • Enantioselective addition of organozinc reagents to aldehydes
    • Soai, K.; Niwa, S. Enantioselective addition of organozinc reagents to aldehydes. Chem. Rev. 1992, 92, 833.
    • (1992) Chem. Rev. , vol.92 , pp. 833
    • Soai, K.1    Niwa, S.2
  • 7
    • 33748247006 scopus 로고
    • Enantioselective addition of organometallic reagents to carbonyl compounds: Chirality transfer, multiplication, and amplification
    • Noyori, R.; Kitamura, M. Enantioselective addition of organometallic reagents to carbonyl compounds: Chirality transfer, multiplication, and amplification. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
    • (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 49
    • Noyori, R.1    Kitamura, M.2
  • 8
    • 0034607311 scopus 로고    scopus 로고
    • Design of diastereomeric self-inhibiting catalysts for control of turnover frequency and enantioselectivity
    • Balsells, J.; Walsh, P. J. Design of diastereomeric self-inhibiting catalysts for control of turnover frequency and enantioselectivity. J. Am. Chem. Soc. 2000, 122, 3250.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 3250
    • Balsells, J.1    Walsh, P.J.2
  • 9
    • 0032485426 scopus 로고    scopus 로고
    • First enantioselective addition of dialkylzinc to ketones promoted by titanium (IV) derivatives
    • Ramon, D. J.; Yus, M. First enantioselective addition of dialkylzinc to ketones promoted by titanium (IV) derivatives. Tetrahedron Lett. 1998, 39, 1239.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1239
    • Ramon, D.J.1    Yus, M.2
  • 11
    • 84987254276 scopus 로고
    • Enantioselective addition of diethylzinc to aldehydes in the presence of chiral titanium reagent modified with n-sulfonylated amino alcohol
    • Ito, K.; Kimura, Y.; Okamura, H.; Katsuki, T. Enantioselective addition of diethylzinc to aldehydes in the presence of chiral titanium reagent modified with n-sulfonylated amino alcohol. Synlett 1992, 573.
    • (1992) Synlett , vol.573
    • Ito, K.1    Kimura, Y.2    Okamura, H.3    Katsuki, T.4
  • 12
    • 10844234849 scopus 로고    scopus 로고
    • Concise synthesis of novel practical sulfamide-amine alcohols for the enantioselective addition of diethylzinc to aldehydes
    • Mao, J.; Wan, B.; Wang, R.; Wu, F.; Lu, S. Concise synthesis of novel practical sulfamide-amine alcohols for the enantioselective addition of diethylzinc to aldehydes. J. Org. Chem. 2004, 69, 9123.
    • (2004) J. Org. Chem. , vol.69 , pp. 9123
    • Mao, J.1    Wan, B.2    Wang, R.3    Wu, F.4    Lu, S.5
  • 13
    • 9944250955 scopus 로고    scopus 로고
    • 4: Novel sulfamide-amine alcohol ligands for the catalytic asymmetric addition of diethylzinc to aldehydes
    • Mao, J.; Wan, B.; Zhang, Z.; Wang, R.; Wu, F.; Lu, S. Reversal of enantioselectivity by adding Ti(OiPr)4: Novel sulfamide-amine alcohol ligands for the catalytic asymmetric addition of diethylzinc to aldehydes. J. Mol. Catal. A: Chem. 2005, 225, 33.
    • (2005) J. Mol. Catal. A: Chem. , vol.225 , pp. 33
    • Mao, J.1    Wan, B.2    Zhang, Z.3    Wang, R.4    Wu, F.5    Lu, S.6
  • 14
    • 3342925158 scopus 로고    scopus 로고
    • Short and efficient synthesis of optically active n-tosyl aziridines from 2-amino alcohols
    • Bieber, L. W.; de Araújo, M. C. F. Short and efficient synthesis of optically active n-tosyl aziridines from 2-amino alcohols. Molecules 2002, 7, 902.
    • (2002) Molecules , vol.7 , pp. 902
    • Bieber, L.W.1    De Araújo, M.C.F.2
  • 15
    • 41149115644 scopus 로고    scopus 로고
    • Highly enantioselective alkynylation of aldehydes catalyzed by a new oxazolidine-titanium complex
    • Xu, Z.; Mao, J.; Zhang, Y. Highly enantioselective alkynylation of aldehydes catalyzed by a new oxazolidine-titanium complex. Org. Biomol. Chem. 2008, 6, 1288
    • (2008) Org. Biomol. Chem. , vol.6 , pp. 1288
    • Xu, Z.1    Mao, J.2    Zhang, Y.3
  • 16
    • 25444519747 scopus 로고    scopus 로고
    • First example of asymmetric transfer hydrogenation in water induced by a chiral amino alcohol hydrochloride
    • Mao, J.; Wan, B.; Wu, F.; Lu, S. First example of asymmetric transfer hydrogenation in water induced by a chiral amino alcohol hydrochloride. Tetrahedron Lett. 2005, 46, 7341
    • (2005) Tetrahedron Lett. , vol.46 , pp. 7341
    • Mao, J.1    Wan, B.2    Wu, F.3    Lu, S.4
  • 17
    • 21644463030 scopus 로고    scopus 로고
    • Sulfamide-amine alcohol catalyzed enantioselective alkynylation of aromatic ketones
    • Mao, J.; Wan, B.; Wu, F.; Wang, R.; Lu, S. Sulfamide-amine alcohol catalyzed enantioselective alkynylation of aromatic ketones. J. Mol. Catal. A: Chem. 2005, 237, 126
    • (2005) J. Mol. Catal. A: Chem. , vol.237 , pp. 126
    • Mao, J.1    Wan, B.2    Wu, F.3    Wang, R.4    Lu, S.5
  • 18
    • 18144394295 scopus 로고    scopus 로고
    • Readily available sulfamide-amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(OiPr)4
    • Mao, J.; Wan, B.; Wu, F.; Lu, S. Readily available sulfamide-amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(OiPr)4. Chirality 2005, 17, 245.
    • (2005) Chirality , vol.17 , pp. 245
    • Mao, J.1    Wan, B.2    Wu, F.3    Lu, S.4
  • 19
    • 0345711474 scopus 로고    scopus 로고
    • Towards perfect asymmetric catalysis: Additives and cocatalysts
    • Vogl, E. M.; Groger, H.; Shibasaki, M. Towards perfect asymmetric catalysis: additives and cocatalysts. Angew. Chem. Int. Ed. 1999, 38, 1570.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1570
    • Vogl, E.M.1    Groger, H.2    Shibasaki, M.3
  • 20
    • 0037132590 scopus 로고    scopus 로고
    • Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source
    • Bolm, C.; Rudolph, J. Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source. J. Am. Chem. Soc. 2002, 124, 14850.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 14850
    • Bolm, C.1    Rudolph, J.2
  • 21
    • 0032581998 scopus 로고    scopus 로고
    • Quantitative analysis of the chiral amplification in the amino alcohol-promoted asymmetric alkylation of aldehydes with dialkylzincs
    • Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. Quantitative analysis of the chiral amplification in the amino alcohol-promoted asymmetric alkylation of aldehydes with dialkylzincs. J. Am. Chem. Soc. 1998, 120, 9800.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 9800
    • Kitamura, M.1    Suga, S.2    Oka, H.3    Noyori, R.4
  • 22
    • 0000414234 scopus 로고    scopus 로고
    • Asymmetric addition of dimethylzinc to benzal-dehyde catalyzed by (2S)-3-exo-(dimethylamino)isobornenol: A theoretical study on the origin of enantioselection
    • Yamakawa, M.; Noyori, R. Asymmetric addition of dimethylzinc to benzal-dehyde catalyzed by (2S)-3-exo-(dimethylamino)isobornenol: A theoretical study on the origin of enantioselection. Organometallics 1999, 18, 128.
    • (1999) Organometallics , vol.18 , pp. 128
    • Yamakawa, M.1    Noyori, R.2
  • 23
    • 33646462433 scopus 로고    scopus 로고
    • De novo chiral amino alcohols in catalyzing asymmetric additions to aryl aldehydes
    • Huang, J.; Lanni, J. C.; Antoline, J. E.; Hsung, R. P.; Kozlowski, M.C. De novo chiral amino alcohols in catalyzing asymmetric additions to aryl aldehydes. Org. Lett. 2006, 8, 1565.
    • (2006) Org. Lett. , vol.8 , pp. 1565
    • Huang, J.1    Lanni, J.C.2    Antoline, J.E.3    Hsung, R.P.4    Kozlowski, M.C.5
  • 24
    • 0037473518 scopus 로고    scopus 로고
    • Modeling the stereoselectivity of the b-amino alcohol-promoted addition of dialkylzinc to aldehydes
    • Rasmussen, T.; Norrby, P. O. Modeling the stereoselectivity of the b-amino alcohol-promoted addition of dialkylzinc to aldehydes. J. Am. Chem. Soc. 2003, 125, 5130.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 5130
    • Rasmussen, T.1    Norrby, P.O.2
  • 25
    • 0034602444 scopus 로고    scopus 로고
    • A quantum mechanics=molecular mechanics study of the highly enantioselective addition of diethylzinc to benzaldehyde promoted by (R)-2-piperidino-1,1,2-triphenylethanol
    • Vazquez, J.; Pericas, M. A.; Maseras, F.; Lledos, A. A quantum mechanics=molecular mechanics study of the highly enantioselective addition of diethylzinc to benzaldehyde promoted by (R)-2-piperidino-1,1,2-triphenylethanol. J. Org. Chem. 2000, 65, 7303.
    • (2000) J. Org. Chem. , vol.65 , pp. 7303
    • Vazquez, J.1    Pericas, M.A.2    Maseras, F.3    Lledos, A.4
  • 26
    • 0031791876 scopus 로고    scopus 로고
    • Origin of enantioselectivities in chiral b-amino alcohol catalyzed asymmetric additions of organozinc reagents to benzalde-hyde: PM3 transition state modeling
    • Goldfuss, B.; Houk, K. N. Origin of enantioselectivities in chiral b-amino alcohol catalyzed asymmetric additions of organozinc reagents to benzalde-hyde: PM3 transition state modeling. J. Org. Chem. 1998, 63, 8998.
    • (1998) J. Org. Chem. , vol.63 , pp. 8998
    • Goldfuss, B.1    Houk, K.N.2
  • 27
    • 0000298661 scopus 로고    scopus 로고
    • Synthesis and crystal structures of chiral titanium bis(sulfonamido) bis(amide) complexes: Differences in ligand hapticity caused by crystal packing forces
    • Pritchett, S.; Gantzel, P.; Walsh, P. J. Synthesis and crystal structures of chiral titanium bis(sulfonamido) bis(amide) complexes: Differences in ligand hapticity caused by crystal packing forces. Organometallics 1997, 16, 5130.
    • (1997) Organometallics , vol.16 , pp. 5130
    • Pritchett, S.1    Gantzel, P.2    Walsh, P.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.