Details
| Original language | English |
|---|---|
| Pages (from-to) | 9433-9440 |
| Number of pages | 8 |
| Journal | Journal of Organic Chemistry |
| Volume | 68 |
| Issue number | 24 |
| Publication status | Published - 28 Nov 2003 |
| Externally published | Yes |
Abstract
A simple and high-yielding method for the preparation of cyclopropane amino acids is described. The novel method involves the one-pot cyclopropanation of readily available dehydroamino acids using aryl and unsaturated diazo compounds generated in situ from the corresponding tosylhydrazone salts. It was found that thermal 1,3-dipolar cycloaddition followed by nitrogen extrusion gave the cyclopropane amino acid derivatives with good E selectivity, while reactions in the presence of meso-tetraphenylporphyrin iron chloride gave predominantly the corresponding Z isomers. The synthetic utility of this process was demonstrated in the synthesis of (±)-(Z)-2,3-methanophenylalanine [(±)-(Z)-1], the anti-Parkinson (±)-(E)-2,3-methano-m-tyrosine [(±)-(E)-2], and the natural product (±)-coronamic acid [(±)-3].
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: Journal of Organic Chemistry, Vol. 68, No. 24, 28.11.2003, p. 9433-9440.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Diastereoselective Synthesis of Cyclopropane Amino Acids Using Diazo Compounds Generated in Situ
AU - Adams, Luke A.
AU - Aggarwal, Varinder K.
AU - Bonnert, Roger V.
AU - Bressel, Bettina
AU - Cox, Russell J.
AU - Shepherd, Jon
AU - De Vicente, Javier
AU - Walter, Magnus
AU - Whittingham, William G.
AU - Winn, Caroline L.
PY - 2003/11/28
Y1 - 2003/11/28
N2 - A simple and high-yielding method for the preparation of cyclopropane amino acids is described. The novel method involves the one-pot cyclopropanation of readily available dehydroamino acids using aryl and unsaturated diazo compounds generated in situ from the corresponding tosylhydrazone salts. It was found that thermal 1,3-dipolar cycloaddition followed by nitrogen extrusion gave the cyclopropane amino acid derivatives with good E selectivity, while reactions in the presence of meso-tetraphenylporphyrin iron chloride gave predominantly the corresponding Z isomers. The synthetic utility of this process was demonstrated in the synthesis of (±)-(Z)-2,3-methanophenylalanine [(±)-(Z)-1], the anti-Parkinson (±)-(E)-2,3-methano-m-tyrosine [(±)-(E)-2], and the natural product (±)-coronamic acid [(±)-3].
AB - A simple and high-yielding method for the preparation of cyclopropane amino acids is described. The novel method involves the one-pot cyclopropanation of readily available dehydroamino acids using aryl and unsaturated diazo compounds generated in situ from the corresponding tosylhydrazone salts. It was found that thermal 1,3-dipolar cycloaddition followed by nitrogen extrusion gave the cyclopropane amino acid derivatives with good E selectivity, while reactions in the presence of meso-tetraphenylporphyrin iron chloride gave predominantly the corresponding Z isomers. The synthetic utility of this process was demonstrated in the synthesis of (±)-(Z)-2,3-methanophenylalanine [(±)-(Z)-1], the anti-Parkinson (±)-(E)-2,3-methano-m-tyrosine [(±)-(E)-2], and the natural product (±)-coronamic acid [(±)-3].
UR - http://www.scopus.com/inward/record.url?scp=10744224646&partnerID=8YFLogxK
U2 - 10.1021/jo035060c
DO - 10.1021/jo035060c
M3 - Article
C2 - 14629169
AN - SCOPUS:10744224646
VL - 68
SP - 9433
EP - 9440
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 24
ER -