Please read my paper on the Tetrahedron, It focused on reduction of simple imine with a lewis base catalysts.

aNatural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China

bDepartment of Chemistry, Xihua University, Chengdu 610039, China

Received 23 April 2008;
revised 2 September 2008;
accepted 5 September 2008.
Available online 23 September 2008.

Abstract

l-Pipecolinic acid derived N-formamides have been developed as new Lewis basic organocatalysts that promote the asymmetric reduction of N-aryl ketimines using trichlorosilane as the reducing agent. The substituent on N4 of the piperazinyl backbone and the 2-carboxamide group both proved to have profound effects on the efficacy of the catalyst. The reductions of both N-aryl acyclic methyl ketimines and non-methyl ketimines were catalyzed to afford the desired amines in good to high yield and enantioselectivity. In particular, catalyst 6e enabled the reduction of the difficult bulky ketimines to be highly efficient and enantioselective, affording up to 99% yield and 97% ee. This catalyst proved to prefer the relatively bulkier non-methyl acyclic ketimines to the methyl ketimines as substrate, which is so far unprecedented in catalytic asymmetric reduction of imines.

Keywords: Lewis basic organocatalysts; Acyclic ketimines; l-Pipecolinic acid; Asymmetric reduction
Article Outline

1. Introduction
2. Result and discussion

2.1. Catalyst design and synthesis
2.2. Asymmetric reduction of ketimines with HSiCl3 catalyzed by chiral formamides
2.3. Mechanistic consideration

3. Conclusion
4. Experimental

4.1. General methods
4.2. General procedure for the synthesis of imines

4.2.1. Imine 1c
4.2.2. Imine 1d
4.2.3. Imine 1e
4.2.4. Imine 1f
4.2.5. Imine 1g
4.2.6. Imine 1h
4.2.7. Imine 1l
4.2.8. Imine 1m
4.2.9. Imine 1n

4.3. General procedure for catalytic hydrosilylation of imines

4.3.1. Amine 2a
4.3.2. Amine 2b
4.3.3. Amine 2c
4.3.4. Amine 2d
4.3.5. Amine 2e
4.3.6. Amine 2f
4.3.7. Amine 2g
4.3.8. Amine 2h
4.3.9. Amine 2i
4.3.10. Amine 2j
4.3.11. Amine 2k
4.3.12. Amine 2l
4.3.13. Amine 2m
4.3.14. Amine 2n

4.4. General procedure for the synthesis of catalysts 6, 9, and 10

4.4.1. Catalyst 6a
4.4.2. Catalyst 6b
4.4.3. Catalyst 6c
4.4.4. Catalyst 6d
4.4.5. Catalyst 6e
4.4.6. Catalyst 6f
4.4.7. Catalyst 6g
4.4.8. Catalyst 6h
4.4.9. Catalyst 9a
4.4.10. Catalyst 9b
4.4.11. Catalyst 9c
4.4.12. Catalyst 9d
4.4.13. Catalyst 9e
4.4.14. Catalyst 9f
4.4.15. Catalyst 9g
4.4.16. Catalyst 9h
4.4.17. Catalyst 10a
4.4.18. Catalyst 10b

4.5. General procedure for the synthesis of catalysts 7 and 8

4.5.1. Catalyst 7a
4.5.2. Catalyst 7b
4.5.3. Catalyst 7c
4.5.4. Catalyst 8a
4.5.5. Catalyst 8b
4.5.6. Catalyst 8c

Acknowledgements
References

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