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Volumn 33, Issue 41, 1992, Pages 6127-6130

A simple and general method for the asymmetric synthesis of α-aminophosphonic acids

a CNRS (France)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE; PHOSPHONOAMINO ACID;

ARTICLE; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0026663281 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)60023-0 Document Type: Article

Times cited : (41)

References (24)

1
- 0000899405
- OPTICALLY ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDS
- and references cited herein
- (1987) Phosphorus, Sulfur, and Silicon and the Related Elements , vol.30 , pp. 119
- Dhawan¹ Redmore²

2
- 33751554378
- (1990) J. Org. Chem. , vol.55 , pp. 6268
- Bartlett¹ Hanson² Giannousis³

4
- 0007929196
- Absolute Configuration of optically active aminophosphonic acids
- (1977) Tetrahedron Letters , pp. 3965
- Glowiak¹ Sawka-Dobrowolska² Kowalik³ Mastalerz⁴ Soroka⁵ Zon⁶

6
- 84985087355
- (1982) Helv. Chim. Acta , vol.65 , pp. 1953
- Vasella¹ Voeffray²

7
- 84987480058
- Nucleophilic Additions toN-Glycosylnitrones. Asymmetric Synthesis of ?-Aminophosphonic Acids
- (1985) Helvetica Chimica Acta , vol.68 , pp. 1730
- Huber¹ Knierzinger² Obrecht³ Vasella⁴

8
- 84985186249
- Asymmetric synthesis of α-aminophosphonic acids, I enantioselective synthesis of L-(1-aminoethyl)phosphonic acid by asymmetric catalytic hydrogenation ofN-[1-(dimethoxyphosphoryl)ethenyl]formamide
- (1985) Liebigs Annalen der Chemie , pp. 555
- Schöllkopf¹ Hoppe² Thiele³

10
- 0343322723
- DIASTEREOSELECTIVITY IN THE ALKYLATION OF CHIRAL 2-AMINOMETHYL-1,3,2-DIOXAPHOSPHORINANE 2-OXIDES
- (1987) Phosphorous and Sulfur and the Related Elements , vol.33 , pp. 1
- Bartlett¹ McLaren²

11
- 84985225807
- Asymmetrische Synthese von α-Aminophosphonsäuren, III. Asymmetrische Synthese von (S)-(1-Aminoalkyl)phosphonsäure-diethylestern unter Verwendung von (+)-Campher als chiralem Hilfsreagens
- (1987) Liebigs Annalen der Chemie , pp. 45
- Schöllkopf¹ Schütze²

12
- 0002714199
- SYNTHESIS OF ENANTIOMERICALLY PURE AMINOPHOSPHONIC ACIDS
- (1998) Phosphorous and Sulfur and the Related Elements , vol.36 , pp. 73
- Jacquier¹ Ouazzani² Roumestant³ Viallefont⁴

14
- 0024544078
- (1989) Tetrahedron Lett. , vol.30 , pp. 2247
- Sawamura¹ Ito² Hayashi³

15
- 84986691327
- Phosphoranaloge von Aminosäuren III1. Synthese optisch aktiver 1-Aminoalkylphosphonsäuren der (S)- und (R)-Reihe mit Hilfe von (-)-Ephedrin als Auxiliar
- (1990) Synthesis , pp. 132
- Sting¹ Steglich²

16
- 0025187520
- (1990) Tetrahedron Lett. , vol.31 , pp. 6465
- Hanessian¹ Bennani²

18
- 0026551174
- (1992) Tetrahedron Asymmetry , vol.3 , pp. 377
- Yokomatsu¹ Shibuya²

19
- 0000030142
- (1985) Tetrahedron Lett. , vol.26 , pp. 3567
- Marco¹ Royer² Husson³

20
- 84919197346
- 4) and evaporated under vacuum to give a white crystalline compound which was recrystallized from ether ( 17.6 g; 65% yield).

21
- 84919197345
- Attempts to deprotonate phosphonate 4 using LDA (1–4 eq.), KHMDS or NAHMDS (2 eq.), n-BuLi (1–3 eq.) or 1 eq. t-BuLi proved unsuccessful.

22
- 84919197344
- In a typical experiment t-BuLi (1.5 M in pentane, 1.6 mmol) was added to a solution of phosphonate 4 (0.75 mmol) in dry THF (10 mL) cooled at −78°C. After 20 min alkyl halide (8 mmol) was added to the yellow solution. The reaction was quenched with water after disappearance of starting material (ca 30 min) and then allowed to warm to room temperature. Flash-chromatography of the crude mixture afforded the α-alkylated compound (yield 60–85% see Table).

23
- 0000726942
- Optically active 1-aminoalkanephosphonic acids. Dibenzoyl-L-tartaric anhydride as an effective agent for the resolution of racemic diphenyl 1-aminoalkanephosphonates
- (1983) Canadian Journal of Chemistry , vol.61 , pp. 2425
- Kafarski¹ Lejczak² Szewczyk³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.