Full Paper

Synthesis of Stereoisomers of 3-Aminocyclohexanecarboxylic Acid and cis-3-Aminocyclohexene-5-carboxylic Acid

Yu Hu

Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province at Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China

Graduate School of Chinese Academy of Sciences, Beijing 100039, China

Search for more papers by this author

Sheng-Liang Yu,

Sheng-Liang Yu

Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province at Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China

Search for more papers by this author

Yu-Jin Yang,

Yu-Jin Yang

Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province at Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China

Graduate School of Chinese Academy of Sciences, Beijing 100039, China

Search for more papers by this author

Jin Zhu,

Jin Zhu

[email protected]

Project supported by the National Natural Science Foundation of China (Nos. 20172050, 20025205).

Tel.: 0086-28-85229689; Fax: 0086-28-85223978

Search for more papers by this author

Jin-Gen Deng,

Jin-Gen Deng

Search for more papers by this author

Yu Hu,

Yu Hu

Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province at Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China

Graduate School of Chinese Academy of Sciences, Beijing 100039, China

Search for more papers by this author

Sheng-Liang Yu,

Sheng-Liang Yu

Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province at Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China

Search for more papers by this author

Yu-Jin Yang,

Yu-Jin Yang

Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province at Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China

Graduate School of Chinese Academy of Sciences, Beijing 100039, China

Search for more papers by this author

Jin Zhu,

Jin Zhu

[email protected]

Project supported by the National Natural Science Foundation of China (Nos. 20172050, 20025205).

Tel.: 0086-28-85229689; Fax: 0086-28-85223978

Search for more papers by this author

Jin-Gen Deng,

Jin-Gen Deng

Search for more papers by this author

First published: 07 June 2006

https://doi.org/10.1002/cjoc.200690151

Citations: 22

Project supported by the National Natural Science Foundation of China (Nos. 20172050, 20025205).

Tel.: 0086-28-85229689; Fax: 0086-28-85223978

About

PDF

Tools

Share a link

Email
Wechat
Bluesky

Abstract

A practical synthesis of stereoisomers of 3-aminocyclohexanecarboxylic acid and cis-3-aminocyclohexene-5- carboxylic acid was achieved from cyclohexene-4-carboxylic acid via a key resolving approach with chiral 1-phenylethylamine.

REFERENCES

1 Creighton, T. E., Proteins: Structures and Molecular Properties, 2nd ed., Freeman, New York, 1993.
Google Scholar
2 Seebach, D.; Schaeffer, L.; Brenner, M.; Hoyer, D.. Angew. Chem., Int. Ed., 2003, 42, 776 and references therein.
10.1002/anie.200390205
CAS PubMed Web of Science® Google Scholar
3 Josep, F. S.; Laura, Z.; David, V.; Xavier, S.; Emest, G.; Miquel, P.; Fernando, A.; Miriam, R.. J. Am. Chem. Soc., 2004, 126, 6048 and references therein.
10.1021/ja0398621
CAS PubMed Web of Science® Google Scholar
4 Amorin, M.; Castedo, L.; Granja, J. R.. J. Am. Chem. Soc., 2003, 125, 2844 and references therein.
10.1021/ja0296273
CAS PubMed Web of Science® Google Scholar
5 Schousboe, A.. Neurochem. Res., 2000, 25, 1241.
10.1023/A:1007692012048
CAS PubMed Web of Science® Google Scholar
6 Roberts, E.; Chase, T. N.; Towes, D. B., GABA in Nervous System Function, Raven Press, New York, 1976.
Google Scholar
7 Allan, R. D.; Johnston, G. A. R.; Twitchin, B.. Aust. J. Chem., 1981, 34, 2231.
10.1071/CH9812231
CAS Web of Science® Google Scholar
8 Choi, S.; Silverman, R. B.. J. Med. Chem., 2002, 45, 4531.
10.1021/jm020134i
CAS PubMed Web of Science® Google Scholar
9 Choi, S.; Storici, P.; Schirmer, T.; Silverman, R. B.. J. Am. Chem. Soc., 2002, 124, 1620.
10.1021/ja011968d
CAS PubMed Web of Science® Google Scholar
10 Murahashi, S. I.; Taniguchi, Y.; Imada, Y.; Tanigawa, Y.. J. Org. Chem., 1989, 54, 3292.
10.1021/jo00275a011
CAS Web of Science® Google Scholar
11 Trost, B. M.; Kondo, Y.. Tetrahedron Lett., 1991, 13, 1613.
10.1016/S0040-4039(00)74285-7
Web of Science® Google Scholar
12 Kato, M.; Kageyama, M.; Tanaka, R.; Kuwahara, K.; Yoshikoshi, A.. J. Org. Chem., 1975, 40, 1932.
10.1021/jo00901a014
CAS Web of Science® Google Scholar
13 Grewe, R.; Heinke, A.; Sommer, C.. Chem. Ber., 1956, 89, 1978.
10.1002/cber.19560890827
CAS Web of Science® Google Scholar
14 Ceder, O.; Hansson, B.. Acta Chem. Scand., 1970, 24, 2693.
10.3891/acta.chem.scand.24-2693
CAS Web of Science® Google Scholar
15 Woll, M. G.; Lai, J. R.; Guzei, I. A.; Taylor, S. J. C.; Smith, M. E. B.; Gellman, S. H.. J. Am. Chem. Soc., 2001, 123, 11077.
10.1021/ja011719p
CAS PubMed Web of Science® Google Scholar
16 Bong, D. T.; Clark, T. D.; Granja, J. R.; Ghadiri, M. R.. Angew. Chem., Int. Ed., 2001, 40, 988.
10.1002/1521-3773(20010316)40:6<988::AID-ANIE9880>3.0.CO;2-N
CAS PubMed Web of Science® Google Scholar

Citing Literature

Volume24, Issue6

June, 2006

Pages 795-799

Synthesis of Stereoisomers of 3-Aminocyclohexanecarboxylic Acid and cis-3-Aminocyclohexene-5-carboxylic Acid

Abstract

REFERENCES

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Synthesis of Stereoisomers of 3-Aminocyclohexanecarboxylic Acid and cis-3-Aminocyclohexene-5-carboxylic Acid

Abstract

REFERENCES

Citing Literature

References

Related

Information