No.107
Chiral β-Amino Alcohol
| P1375 | (1S,2R)-1-Phenyl-2-(1-pyrrolidinyl)propan-1-ol (1a) |
1g |
| P1374 | (1R,2S)-1-Phenyl-2-(1-pyrrolidinyl)propan-1-ol (1b) |
1g |


Chiral β-amino alcohols 1a and 1b, developed by K. Soai and co-workers, are useful chiral catalysts for enantioselective addition of dialkylzinc compounds to aliphatic,1a) aromatic1b) and five-membered heterocyclic1c) aldehydes. This addition method with 1 affords secondary alcohols 2 with high optical purity.1) Moreover, 1b as a chiral ligand was applied to the enantioselective ketone alkynylation reaction, which is a key step in synthesis of Efavirenz.2) Efavirenz is HIV reverse transcriptase inhibitor.
References
1) Asymmetric alkylation of aldehydes
a) K. Soai, S. Yokoyama, T. Hayasaka, J. Org. Chem., 56, 4264 (1991).
b) K. Soai, T. Konishi, T. Shibata, Heterocycles, 51, 1421 (1999).
c) I. Sato, T. Saito, D. Omiya, Y. Takizawa, K. Soai, ibid., 51, 2753 (1999).
2) Enantioselective alkynylation of ketoaniline
L. Tan, C.-y. Chen, R. D. Tillyer, E. J. J. Grabowski, P. J. Reider, Angew. Chem. Int. Ed., 38, 711 (1999).
A. S. Thompson, E. G. Corley, M. F. Huntington, E. J. J. Grabowski, Tetrahedron Lett., 36, 8937 (1995).
A. Thompson, E. G. Corley, M. F. Huntington, E. J. J. Grabowski, J. F. Remenar, D. B. Collum, J. Am. Chem. Soc., 120, 2028 (1998).
a) K. Soai, S. Yokoyama, T. Hayasaka, J. Org. Chem., 56, 4264 (1991).
b) K. Soai, T. Konishi, T. Shibata, Heterocycles, 51, 1421 (1999).
c) I. Sato, T. Saito, D. Omiya, Y. Takizawa, K. Soai, ibid., 51, 2753 (1999).
2) Enantioselective alkynylation of ketoaniline
L. Tan, C.-y. Chen, R. D. Tillyer, E. J. J. Grabowski, P. J. Reider, Angew. Chem. Int. Ed., 38, 711 (1999).
A. S. Thompson, E. G. Corley, M. F. Huntington, E. J. J. Grabowski, Tetrahedron Lett., 36, 8937 (1995).
A. Thompson, E. G. Corley, M. F. Huntington, E. J. J. Grabowski, J. F. Remenar, D. B. Collum, J. Am. Chem. Soc., 120, 2028 (1998).
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