Parallel Recognition by Kinetic Control with Imino Aldehyde Substrates that are Prone to Redistribution

Advanced Synthesis and Catalysis

Volumn 344, Issue 5, 2002, Pages 548-555

  Orita, Akihiro ^a   Nagano, Yoshifumi ^a   Nakazawa, Koichi ^a   Otera, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Aldehydes; Allylation; Cycloaddition; Lewis acids; Synthetic method

Indexed keywords

EID: 0013117187     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200207)344:5<548::AID-ADSC548>3.0.CO;2-A     Document Type: Article

References (10)

1. a) J. Chen, J. Otera, Angew. Chem. 1998, 110, 96; Angew. Chem. Int. Ed. 1998, 37, 91;
2. a) J. Chen, J. Otera, Angew. Chem. 1998, 110, 96; Angew. Chem. Int. Ed. 1998, 37, 91;
3. b) J. Chen. J. Otera, Tetrahedron Lett. 1998, 39, 1767;
4. c) J. Chen, K. Sakamoto, A. Orita, J. Otera, Tetrahedron 1998, 54, 8411.
5. [3].
6. [3].
7. Mention was made in this relation by Vedejs et al. in their paper on parallel kinetic resolution as "In principle, mixtures of two achiral components (diastereomers; regioisomers; etc.) could also be derivatized with improved efficiency using two complementary reagents in parallel if they react selectively with each isomer to afford a distinct product": E. Vedejs, X. Chen, J. Am. Chem. Soc. 1997, 119, 2584.
8. S. Kobayashi, M. Araki, H. Ishitani, S. Nagayama, I. Hachiya, Synlett 1995, 233.
9. I. Hachiya, S. Kobayashi, J. Org. Chem. 1993, 58, 6958.
10. 2 can quench the reaction instantaneously to allow the quantitative analysis. Note that addition of excess hydrazine induces conversion of the imine to the hydrazone, too.