Stereoselective formation of N-acyliminium ion via chiral N,O-acetal TMS ether and its application to the synthesis of β-amino acids

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3635-3638

  Shin, Dong Yun ^a   Jung, Jae Kyung ^b   Seo, Seung Yong ^a   Lee, Yong Sil ^a   Paek, Seung Mann ^a   Chung, Young Keun ^a   Shin, Dong Mok ^a   Suh, Young Ger ^a  

^a Seoul National University   (South Korea)

^b Chungbuk National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; AMINO ACID; BETA AMINO ACID; CATION; ETHER; ETHER DERIVATIVE; IMINE; OXAZOLIDINE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ACYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; CHIRALITY; GEOMETRY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ACETALS; ACYLATION; AMINO ACIDS; CATIONS; CRYSTALLOGRAPHY, X-RAY; ETHERS; IMINES; MOLECULAR STRUCTURE; OXAZOLIDINONES; STEREOISOMERISM; TRIMETHYLSILYL COMPOUNDS;

EID: 0142011131     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035289e     Document Type: Article

References (23)

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4. For recent reports about the asymmetric synthesis of β-amino acids utilizing imine species, see: (a) Murahashi, S.; Imada, Y.; Kawakami, T.; Harada, K.; Yonemushi, Y.; Tomita, N. J. Am. Chem. Soc. 2002, 124, 2888. (b) Moglioni, A. G.; Muray, E.; Castillo, J. A.; Alvarez-Larena, A.; Moltrasio, G. Y.; Branchadell, V.; Ortuno, R. M. J. Org. Chem. 2002, 67, 2402. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. (d) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (e) Kise, N.; Uena, N. Org. Lett. 1999, 1, 1803. (f) Muller, R.; Goesmann, H.; Waldmann, H. Angew. Chem., Int. Ed. 1999, 37, 184 and related references are therein.
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7. For recent reports about the asymmetric synthesis of β-amino acids utilizing imine species, see: (a) Murahashi, S.; Imada, Y.; Kawakami, T.; Harada, K.; Yonemushi, Y.; Tomita, N. J. Am. Chem. Soc. 2002, 124, 2888. (b) Moglioni, A. G.; Muray, E.; Castillo, J. A.; Alvarez-Larena, A.; Moltrasio, G. Y.; Branchadell, V.; Ortuno, R. M. J. Org. Chem. 2002, 67, 2402. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. (d) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (e) Kise, N.; Uena, N. Org. Lett. 1999, 1, 1803. (f) Muller, R.; Goesmann, H.; Waldmann, H. Angew. Chem., Int. Ed. 1999, 37, 184 and related references are therein.
8. For recent reports about the asymmetric synthesis of β-amino acids utilizing imine species, see: (a) Murahashi, S.; Imada, Y.; Kawakami, T.; Harada, K.; Yonemushi, Y.; Tomita, N. J. Am. Chem. Soc. 2002, 124, 2888. (b) Moglioni, A. G.; Muray, E.; Castillo, J. A.; Alvarez-Larena, A.; Moltrasio, G. Y.; Branchadell, V.; Ortuno, R. M. J. Org. Chem. 2002, 67, 2402. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. (d) Kobayashi, S.; Matsubara, R.; Kitagawa, H. Org. Lett. 2002, 4, 143. (e) Kise, N.; Uena, N. Org. Lett. 1999, 1, 1803. (f) Muller, R.; Goesmann, H.; Waldmann, H. Angew. Chem., Int. Ed. 1999, 37, 184 and related references are therein.
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22. 2 in the absence of the nucleophiles. We thank the referees for their valuable advice on the mechanistic aspects.
23. 2 workstation.