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Volumn 70, Issue 4, 2005, Pages 1281-1290

Chirality and fragrance chemistry: Stereoisomers of the commercial chiral odorants muguesia and pamplefleur

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ENZYMES; ISOMERS; MIXING; ODORS;

EID: 13844313024     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048445j     Document Type: Article
Times cited : (66)

References (44)
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    • To obtain 1,3-induction two strategies have been optimized: (i) the use of a reducing agent capable of binding the hydroxyl function and of promoting intramolecular hydride transfer; (ii) the use of an additive to preorganize the substrate prior to the addition of the reducing agent which gives intermolecular hydride addition. Examples of the first strategy: (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560. (b) Anwar, S.; Bradley, G.; Davis, A. P. J. Chem. Soc. Perkin Trans. 1 1991, 1383. Examples of the second strategy: (c) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2238. (d) Evans, D. E.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190. (e) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868. (f) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Sambri, L. Chem. Eur. J. 2000, 6, 2590. (g) Bartoli, G.; Bosco, M.; Marcantoni, E.; Massaccesi, M. Rinaldi, S.; Sambri, L. Eur. J. Org. Chem, 2001, 4679;
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    • 37049069121 scopus 로고
    • To obtain 1,3-induction two strategies have been optimized: (i) the use of a reducing agent capable of binding the hydroxyl function and of promoting intramolecular hydride transfer; (ii) the use of an additive to preorganize the substrate prior to the addition of the reducing agent which gives intermolecular hydride addition. Examples of the first strategy: (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560. (b) Anwar, S.; Bradley, G.; Davis, A. P. J. Chem. Soc. Perkin Trans. 1 1991, 1383. Examples of the second strategy: (c) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2238. (d) Evans, D. E.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190. (e) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868. (f) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Sambri, L. Chem. Eur. J. 2000, 6, 2590. (g) Bartoli, G.; Bosco, M.; Marcantoni, E.; Massaccesi, M. Rinaldi, S.; Sambri, L. Eur. J. Org. Chem, 2001, 4679;
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    • To obtain 1,3-induction two strategies have been optimized: (i) the use of a reducing agent capable of binding the hydroxyl function and of promoting intramolecular hydride transfer; (ii) the use of an additive to preorganize the substrate prior to the addition of the reducing agent which gives intermolecular hydride addition. Examples of the first strategy: (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560. (b) Anwar, S.; Bradley, G.; Davis, A. P. J. Chem. Soc. Perkin Trans. 1 1991, 1383. Examples of the second strategy: (c) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2238. (d) Evans, D. E.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190. (e) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868. (f) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Sambri, L. Chem. Eur. J. 2000, 6, 2590. (g) Bartoli, G.; Bosco, M.; Marcantoni, E.; Massaccesi, M. Rinaldi, S.; Sambri, L. Eur. J. Org. Chem, 2001, 4679;
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    • To obtain 1,3-induction two strategies have been optimized: (i) the use of a reducing agent capable of binding the hydroxyl function and of promoting intramolecular hydride transfer; (ii) the use of an additive to preorganize the substrate prior to the addition of the reducing agent which gives intermolecular hydride addition. Examples of the first strategy: (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560. (b) Anwar, S.; Bradley, G.; Davis, A. P. J. Chem. Soc. Perkin Trans. 1 1991, 1383. Examples of the second strategy: (c) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2238. (d) Evans, D. E.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190. (e) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868. (f) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Sambri, L. Chem. Eur. J. 2000, 6, 2590. (g) Bartoli, G.; Bosco, M.; Marcantoni, E.; Massaccesi, M. Rinaldi, S.; Sambri, L. Eur. J. Org. Chem, 2001, 4679;
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    • To obtain 1,3-induction two strategies have been optimized: (i) the use of a reducing agent capable of binding the hydroxyl function and of promoting intramolecular hydride transfer; (ii) the use of an additive to preorganize the substrate prior to the addition of the reducing agent which gives intermolecular hydride addition. Examples of the first strategy: (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560. (b) Anwar, S.; Bradley, G.; Davis, A. P. J. Chem. Soc. Perkin Trans. 1 1991, 1383. Examples of the second strategy: (c) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2238. (d) Evans, D. E.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190. (e) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868. (f) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Sambri, L. Chem. Eur. J. 2000, 6, 2590. (g) Bartoli, G.; Bosco, M.; Marcantoni, E.; Massaccesi, M. Rinaldi, S.; Sambri, L. Eur. J. Org. Chem, 2001, 4679;
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    • 0034679482 scopus 로고    scopus 로고
    • To obtain 1,3-induction two strategies have been optimized: (i) the use of a reducing agent capable of binding the hydroxyl function and of promoting intramolecular hydride transfer; (ii) the use of an additive to preorganize the substrate prior to the addition of the reducing agent which gives intermolecular hydride addition. Examples of the first strategy: (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560. (b) Anwar, S.; Bradley, G.; Davis, A. P. J. Chem. Soc. Perkin Trans. 1 1991, 1383. Examples of the second strategy: (c) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2238. (d) Evans, D. E.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190. (e) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868. (f) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Sambri, L. Chem. Eur. J. 2000, 6, 2590. (g) Bartoli, G.; Bosco, M.; Marcantoni, E.; Massaccesi, M. Rinaldi, S.; Sambri, L. Eur. J. Org. Chem, 2001, 4679;
    • (2000) Chem. Eur. J. , vol.6 , pp. 2590
    • Bartoli, G.1    Bellucci, M.C.2    Bosco, M.3    Dalpozzo, R.4    Marcantoni, E.5    Sambri, L.6
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    • 0035660694 scopus 로고    scopus 로고
    • To obtain 1,3-induction two strategies have been optimized: (i) the use of a reducing agent capable of binding the hydroxyl function and of promoting intramolecular hydride transfer; (ii) the use of an additive to preorganize the substrate prior to the addition of the reducing agent which gives intermolecular hydride addition. Examples of the first strategy: (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560. (b) Anwar, S.; Bradley, G.; Davis, A. P. J. Chem. Soc. Perkin Trans. 1 1991, 1383. Examples of the second strategy: (c) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2238. (d) Evans, D. E.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190. (e) Sarko, C. R.; Collibee, S. E.; Knorr, A. L.; DiMare, M. J. Org. Chem. 1996, 61, 868. (f) Bartoli, G.; Bellucci, M. C.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Sambri, L. Chem. Eur. J. 2000, 6, 2590. (g) Bartoli, G.; Bosco, M.; Marcantoni, E.; Massaccesi, M. Rinaldi, S.; Sambri, L. Eur. J. Org. Chem, 2001, 4679;
    • (2001) Eur. J. Org. Chem , pp. 4679
    • Bartoli, G.1    Bosco, M.2    Marcantoni, E.3    Massaccesi, M.4    Rinaldi, S.5    Sambri, L.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.