Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 542-553 |
| Seitenumfang | 12 |
| Fachzeitschrift | Organic and Biomolecular Chemistry |
| Jahrgang | 2 |
| Ausgabenummer | 4 |
| Publikationsstatus | Veröffentlicht - 21 Feb. 2004 |
| Extern publiziert | Ja |
Abstract
The in situ reaction of protected dehydroamino acids with derivatives of vinyldiazomethane leads to good to excellent yields of vinyl cyclopropanes via 3 + 2 dipolar cycloaddition followed by N 2 extrusion. Chromatographic separation of the cyclopropane diastereomeric products, followed by characterisation by 1H NMR and X-ray crystallography allowed the cis and trans diastereomers to be easily identified. Oxidative cleavage of the vinyl moiety then led directly to protected cyclopropane aspartic acid derivatives in three steps from commercially available materials. These compounds were converted to protected methylenephosphonate, difluoromethylenephosphonate and phosphoramidate analogues of β-aspartyl phosphate.
ASJC Scopus Sachgebiete
- Biochemie, Genetik und Molekularbiologie (insg.)
- Biochemie
- Chemie (insg.)
- Physikalische und Theoretische Chemie
- Chemie (insg.)
- Organische Chemie
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in: Organic and Biomolecular Chemistry, Jahrgang 2, Nr. 4, 21.02.2004, S. 542-553.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Efficient synthesis of protected cyclopropyl β-aspartylphosphates
AU - Adams, Luke A.
AU - Charmant, Jonathan P.H.
AU - Cox, Russell J.
AU - Walter, Magnus
AU - Whittingham, William G.
PY - 2004/2/21
Y1 - 2004/2/21
N2 - The in situ reaction of protected dehydroamino acids with derivatives of vinyldiazomethane leads to good to excellent yields of vinyl cyclopropanes via 3 + 2 dipolar cycloaddition followed by N 2 extrusion. Chromatographic separation of the cyclopropane diastereomeric products, followed by characterisation by 1H NMR and X-ray crystallography allowed the cis and trans diastereomers to be easily identified. Oxidative cleavage of the vinyl moiety then led directly to protected cyclopropane aspartic acid derivatives in three steps from commercially available materials. These compounds were converted to protected methylenephosphonate, difluoromethylenephosphonate and phosphoramidate analogues of β-aspartyl phosphate.
AB - The in situ reaction of protected dehydroamino acids with derivatives of vinyldiazomethane leads to good to excellent yields of vinyl cyclopropanes via 3 + 2 dipolar cycloaddition followed by N 2 extrusion. Chromatographic separation of the cyclopropane diastereomeric products, followed by characterisation by 1H NMR and X-ray crystallography allowed the cis and trans diastereomers to be easily identified. Oxidative cleavage of the vinyl moiety then led directly to protected cyclopropane aspartic acid derivatives in three steps from commercially available materials. These compounds were converted to protected methylenephosphonate, difluoromethylenephosphonate and phosphoramidate analogues of β-aspartyl phosphate.
UR - http://www.scopus.com/inward/record.url?scp=1342323729&partnerID=8YFLogxK
U2 - 10.1039/b311322a
DO - 10.1039/b311322a
M3 - Article
C2 - 14770233
AN - SCOPUS:1342323729
VL - 2
SP - 542
EP - 553
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 4
ER -