anti-Selective asymmetric synthesis of β-hydroxy-α-amino acid esters by the in situ generated chiral quaternary ammonium fluoride-catalyzed mukaiyama-type aldol reaction

Advanced Synthesis and Catalysis

Volumn 346, Issue 9-10, 2004, Pages 1073-1076

  Ooi, Takashi ^a   Taniguchi, Mika ^a   Doda, Kanae ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

hydroxy amino acid; Aldol reaction; Asymmetric synthesis; Chiral quaternary ammonium salt; Diastereoselectivity; Potassium fluoride

Indexed keywords

AMINO ACID DERIVATIVE; FLUORIDE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL ANALYSIS; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MUKAIYAMA REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 5444249237     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.20040111     Document Type: Article

References (48)

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15. For recent representative examples of Sharpless AE, see: T. Nagamitsu, T. Sunazuka, H. Tanaka, S. Omura, P. A. Sprengeler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584; of Sharpless AD, see: H. Shao, J. K. Rueter, M. Goodman, J. Org. Chem. 1998, 63, 5240; of Sharpless AA, see: H. Park, B. Cao, M. M. Joullié, J. Org. Chem. 2001, 66, 7223; of alkylation of β-oxy-α-amino aldehydes, see: N. Okamoto, O. Hara, K. Makino, Y. Hamada, Y. J. Org. Chem. 2002, 67, 9210; of hydrogenation, see: R. Kuwano, S. Okuda, Y. Ito, J. Org. Chem. 1998, 63, 3499; of dynamic kinetic resolution, see: K. Makino, T. Goto, Y. Hiroki, Y. Hamada, Angew. Chem. 2004, 116, 900; Angew. Chem. Int. Ed. 2004, 43, 882; of rearrangements, see: C. Tomashini, A. Vecchione, Org. Lett. 1999, 1, 2153; of selective hydrolysis of aziridine carboxylate, see: F. A. Davis, G. V. Reddy, Tetrahedron Lett. 1996, 37, 4349; of electrophilic animation, see: G. Guanti, L. Banfi, E. Narisano, Tetrahedron 1988, 44, 5553; of the Strecker reaction, see: F. A. Davis, V. Srirajan, D. L. Fanelli, P. Portonovo, J. Org. Chem. 2000, 65, 7663.
16. For recent representative examples of Sharpless AE, see: T. Nagamitsu, T. Sunazuka, H. Tanaka, S. Omura, P. A. Sprengeler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584; of Sharpless AD, see: H. Shao, J. K. Rueter, M. Goodman, J. Org. Chem. 1998, 63, 5240; of Sharpless AA, see: H. Park, B. Cao, M. M. Joullié, J. Org. Chem. 2001, 66, 7223; of alkylation of β-oxy-α-amino aldehydes, see: N. Okamoto, O. Hara, K. Makino, Y. Hamada, Y. J. Org. Chem. 2002, 67, 9210; of hydrogenation, see: R. Kuwano, S. Okuda, Y. Ito, J. Org. Chem. 1998, 63, 3499; of dynamic kinetic resolution, see: K. Makino, T. Goto, Y. Hiroki, Y. Hamada, Angew. Chem. 2004, 116, 900; Angew. Chem. Int. Ed. 2004, 43, 882; of rearrangements, see: C. Tomashini, A. Vecchione, Org. Lett. 1999, 1, 2153; of selective hydrolysis of aziridine carboxylate, see: F. A. Davis, G. V. Reddy, Tetrahedron Lett. 1996, 37, 4349; of electrophilic animation, see: G. Guanti, L. Banfi, E. Narisano, Tetrahedron 1988, 44, 5553; of the Strecker reaction, see: F. A. Davis, V. Srirajan, D. L. Fanelli, P. Portonovo, J. Org. Chem. 2000, 65, 7663.
17. For recent representative examples of Sharpless AE, see: T. Nagamitsu, T. Sunazuka, H. Tanaka, S. Omura, P. A. Sprengeler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584; of Sharpless AD, see: H. Shao, J. K. Rueter, M. Goodman, J. Org. Chem. 1998, 63, 5240; of Sharpless AA, see: H. Park, B. Cao, M. M. Joullié, J. Org. Chem. 2001, 66, 7223; of alkylation of β-oxy-α-amino aldehydes, see: N. Okamoto, O. Hara, K. Makino, Y. Hamada, Y. J. Org. Chem. 2002, 67, 9210; of hydrogenation, see: R. Kuwano, S. Okuda, Y. Ito, J. Org. Chem. 1998, 63, 3499; of dynamic kinetic resolution, see: K. Makino, T. Goto, Y. Hiroki, Y. Hamada, Angew. Chem. 2004, 116, 900; Angew. Chem. Int. Ed. 2004, 43, 882; of rearrangements, see: C. Tomashini, A. Vecchione, Org. Lett. 1999, 1, 2153; of selective hydrolysis of aziridine carboxylate, see: F. A. Davis, G. V. Reddy, Tetrahedron Lett. 1996, 37, 4349; of electrophilic animation, see: G. Guanti, L. Banfi, E. Narisano, Tetrahedron 1988, 44, 5553; of the Strecker reaction, see: F. A. Davis, V. Srirajan, D. L. Fanelli, P. Portonovo, J. Org. Chem. 2000, 65, 7663.
18. For recent representative examples of Sharpless AE, see: T. Nagamitsu, T. Sunazuka, H. Tanaka, S. Omura, P. A. Sprengeler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584; of Sharpless AD, see: H. Shao, J. K. Rueter, M. Goodman, J. Org. Chem. 1998, 63, 5240; of Sharpless AA, see: H. Park, B. Cao, M. M. Joullié, J. Org. Chem. 2001, 66, 7223; of alkylation of β-oxy-α-amino aldehydes, see: N. Okamoto, O. Hara, K. Makino, Y. Hamada, Y. J. Org. Chem. 2002, 67, 9210; of hydrogenation, see: R. Kuwano, S. Okuda, Y. Ito, J. Org. Chem. 1998, 63, 3499; of dynamic kinetic resolution, see: K. Makino, T. Goto, Y. Hiroki, Y. Hamada, Angew. Chem. 2004, 116, 900; Angew. Chem. Int. Ed. 2004, 43, 882; of rearrangements, see: C. Tomashini, A. Vecchione, Org. Lett. 1999, 1, 2153; of selective hydrolysis of aziridine carboxylate, see: F. A. Davis, G. V. Reddy, Tetrahedron Lett. 1996, 37, 4349; of electrophilic animation, see: G. Guanti, L. Banfi, E. Narisano, Tetrahedron 1988, 44, 5553; of the Strecker reaction, see: F. A. Davis, V. Srirajan, D. L. Fanelli, P. Portonovo, J. Org. Chem. 2000, 65, 7663.
19. For recent representative examples of Sharpless AE, see: T. Nagamitsu, T. Sunazuka, H. Tanaka, S. Omura, P. A. Sprengeler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584; of Sharpless AD, see: H. Shao, J. K. Rueter, M. Goodman, J. Org. Chem. 1998, 63, 5240; of Sharpless AA, see: H. Park, B. Cao, M. M. Joullié, J. Org. Chem. 2001, 66, 7223; of alkylation of β-oxy-α-amino aldehydes, see: N. Okamoto, O. Hara, K. Makino, Y. Hamada, Y. J. Org. Chem. 2002, 67, 9210; of hydrogenation, see: R. Kuwano, S. Okuda, Y. Ito, J. Org. Chem. 1998, 63, 3499; of dynamic kinetic resolution, see: K. Makino, T. Goto, Y. Hiroki, Y. Hamada, Angew. Chem. 2004, 116, 900; Angew. Chem. Int. Ed. 2004, 43, 882; of rearrangements, see: C. Tomashini, A. Vecchione, Org. Lett. 1999, 1, 2153; of selective hydrolysis of aziridine carboxylate, see: F. A. Davis, G. V. Reddy, Tetrahedron Lett. 1996, 37, 4349; of electrophilic animation, see: G. Guanti, L. Banfi, E. Narisano, Tetrahedron 1988, 44, 5553; of the Strecker reaction, see: F. A. Davis, V. Srirajan, D. L. Fanelli, P. Portonovo, J. Org. Chem. 2000, 65, 7663.
20. For recent representative examples of Sharpless AE, see: T. Nagamitsu, T. Sunazuka, H. Tanaka, S. Omura, P. A. Sprengeler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584; of Sharpless AD, see: H. Shao, J. K. Rueter, M. Goodman, J. Org. Chem. 1998, 63, 5240; of Sharpless AA, see: H. Park, B. Cao, M. M. Joullié, J. Org. Chem. 2001, 66, 7223; of alkylation of β-oxy-α-amino aldehydes, see: N. Okamoto, O. Hara, K. Makino, Y. Hamada, Y. J. Org. Chem. 2002, 67, 9210; of hydrogenation, see: R. Kuwano, S. Okuda, Y. Ito, J. Org. Chem. 1998, 63, 3499; of dynamic kinetic resolution, see: K. Makino, T. Goto, Y. Hiroki, Y. Hamada, Angew. Chem. 2004, 116, 900; Angew. Chem. Int. Ed. 2004, 43, 882; of rearrangements, see: C. Tomashini, A. Vecchione, Org. Lett. 1999, 1, 2153; of selective hydrolysis of aziridine carboxylate, see: F. A. Davis, G. V. Reddy, Tetrahedron Lett. 1996, 37, 4349; of electrophilic animation, see: G. Guanti, L. Banfi, E. Narisano, Tetrahedron 1988, 44, 5553; of the Strecker reaction, see: F. A. Davis, V. Srirajan, D. L. Fanelli, P. Portonovo, J. Org. Chem. 2000, 65, 7663.
21. For recent representative examples of Sharpless AE, see: T. Nagamitsu, T. Sunazuka, H. Tanaka, S. Omura, P. A. Sprengeler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584; of Sharpless AD, see: H. Shao, J. K. Rueter, M. Goodman, J. Org. Chem. 1998, 63, 5240; of Sharpless AA, see: H. Park, B. Cao, M. M. Joullié, J. Org. Chem. 2001, 66, 7223; of alkylation of β-oxy-α-amino aldehydes, see: N. Okamoto, O. Hara, K. Makino, Y. Hamada, Y. J. Org. Chem. 2002, 67, 9210; of hydrogenation, see: R. Kuwano, S. Okuda, Y. Ito, J. Org. Chem. 1998, 63, 3499; of dynamic kinetic resolution, see: K. Makino, T. Goto, Y. Hiroki, Y. Hamada, Angew. Chem. 2004, 116, 900; Angew. Chem. Int. Ed. 2004, 43, 882; of rearrangements, see: C. Tomashini, A. Vecchione, Org. Lett. 1999, 1, 2153; of selective hydrolysis of aziridine carboxylate, see: F. A. Davis, G. V. Reddy, Tetrahedron Lett. 1996, 37, 4349; of electrophilic animation, see: G. Guanti, L. Banfi, E. Narisano, Tetrahedron 1988, 44, 5553; of the Strecker reaction, see: F. A. Davis, V. Srirajan, D. L. Fanelli, P. Portonovo, J. Org. Chem. 2000, 65, 7663.
22. For recent representative examples of Sharpless AE, see: T. Nagamitsu, T. Sunazuka, H. Tanaka, S. Omura, P. A. Sprengeler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584; of Sharpless AD, see: H. Shao, J. K. Rueter, M. Goodman, J. Org. Chem. 1998, 63, 5240; of Sharpless AA, see: H. Park, B. Cao, M. M. Joullié, J. Org. Chem. 2001, 66, 7223; of alkylation of β-oxy-α-amino aldehydes, see: N. Okamoto, O. Hara, K. Makino, Y. Hamada, Y. J. Org. Chem. 2002, 67, 9210; of hydrogenation, see: R. Kuwano, S. Okuda, Y. Ito, J. Org. Chem. 1998, 63, 3499; of dynamic kinetic resolution, see: K. Makino, T. Goto, Y. Hiroki, Y. Hamada, Angew. Chem. 2004, 116, 900; Angew. Chem. Int. Ed. 2004, 43, 882; of rearrangements, see: C. Tomashini, A. Vecchione, Org. Lett. 1999, 1, 2153; of selective hydrolysis of aziridine carboxylate, see: F. A. Davis, G. V. Reddy, Tetrahedron Lett. 1996, 37, 4349; of electrophilic animation, see: G. Guanti, L. Banfi, E. Narisano, Tetrahedron 1988, 44, 5553; of the Strecker reaction, see: F. A. Davis, V. Srirajan, D. L. Fanelli, P. Portonovo, J. Org. Chem. 2000, 65, 7663.
23. For recent representative examples of Sharpless AE, see: T. Nagamitsu, T. Sunazuka, H. Tanaka, S. Omura, P. A. Sprengeler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584; of Sharpless AD, see: H. Shao, J. K. Rueter, M. Goodman, J. Org. Chem. 1998, 63, 5240; of Sharpless AA, see: H. Park, B. Cao, M. M. Joullié, J. Org. Chem. 2001, 66, 7223; of alkylation of β-oxy-α-amino aldehydes, see: N. Okamoto, O. Hara, K. Makino, Y. Hamada, Y. J. Org. Chem. 2002, 67, 9210; of hydrogenation, see: R. Kuwano, S. Okuda, Y. Ito, J. Org. Chem. 1998, 63, 3499; of dynamic kinetic resolution, see: K. Makino, T. Goto, Y. Hiroki, Y. Hamada, Angew. Chem. 2004, 116, 900; Angew. Chem. Int. Ed. 2004, 43, 882; of rearrangements, see: C. Tomashini, A. Vecchione, Org. Lett. 1999, 1, 2153; of selective hydrolysis of aziridine carboxylate, see: F. A. Davis, G. V. Reddy, Tetrahedron Lett. 1996, 37, 4349; of electrophilic animation, see: G. Guanti, L. Banfi, E. Narisano, Tetrahedron 1988, 44, 5553; of the Strecker reaction, see: F. A. Davis, V. Srirajan, D. L. Fanelli, P. Portonovo, J. Org. Chem. 2000, 65, 7663.
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48. [11]