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Volumn 35, Issue 19, 1994, Pages 3139-3142

Competing OH insertion and β-elimination in rhodium carbenoid reactions; synthesis of 2-alkoxy-3-arylpropanoates

Author keywords

[No Author keywords available]

Indexed keywords

ARYLPROPIONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0028272257 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)76851-1 Document Type: Article

Times cited : (36)

References (19)

1
- 0344535125
- Compounds of type 1 can be prepared via Heck, aldol or olefination sequences, followed by reduction of the resulting double bond. For example, see
- (1988) Heterocycles , vol.27 , pp. 257
- Sakamoto¹ Kondo² Kashiwagi³ Yamanaka⁴

2
- 84982077838
- α-Methoxy-, α-Äthylmercapto- und α-Dimethylamino-acrylester aus substituierten Essigestern mit Aldehyden
- (1967) Justus Liebigs Annalen der Chemie , vol.703 , pp. 37
- Horner¹ Renth²

3
- 0013971764
- and especially
- (1966) Liebigs Ann. Chemie , vol.699 , pp. 53
- Grell¹ Machleidt²

4
- 84912913778
- Hindley, R.M. International Patent Appl., Publication No. WO 9202520, 1992

5
- 0020397038
- For similar reactions of analogues of the chloride 2 with thiols see
- (1982) Chem. Pharm. Bull. , vol.30 , pp. 3563
- Sohda¹ Mizuno² Tawada³ Sugiyama⁴ Fujita⁵ Kawamatsu⁶

7
- 0000866402
- For other examples of rhodium carbenoid mediated OH insertion reaction see
- (1973) Tetrahedron Lett. , pp. 2233
- Paulissen¹ Reimlinger² Hayez³ Hubert⁴ Teyssie⁵

10
- 84912913444
- Perkin Trans. 1
- (1991) J. Chem. Soc. , vol.1
- Davies¹ Moody² Taylor³

11
- 84949890826
- Rhodium(II) Trifluoroacetamide; an Excellent Catalyst for Carbenoid O-H Insertion Reactions
- (1992) Synlett , pp. 975
- Cox¹ Kulagowski² Moody³ Sie⁴

12
- 84981750529
- C-Alkylierung von Silber-diazoessigsäure-äthylester und Silberdiazoketonen mit SN1-aktiven Halogeniden
- The diazoester 4, was used for these experiments since the resulting deuterated ethyl cinnamates are known compounds
- (1969) Chemische Berichte , vol.102 , pp. 488
- Schöllkopf¹ Rieber²

13
- 0015838053
- Stereoselective syntheses of trans- and cis-cinnamic acid esters from the phenylalanine derivatives.
- (1973) Tetrahedron Letters , pp. 4267
- Takamura¹ Mizoguchi² Yamada³

15
- 0000768901
- and references therein
- (1992) J. Org. Chem. , vol.57 , pp. 436
- Taber¹ Hennessy² Louey³

16
- 84912932234
- Of the catalysts used only that derived from naphthalene-2-carboxylic acid is a new compound; all catalysts were prepared from rhodium(II) acetate by ligand exchange in the usual way.

17
- 37049098804
- Rearrangement of carboxylates derived from N-acetyl-N-nitroso -?-amino-acids
- Ethyl 2-hydroxy-3-phenylpropanoate 6 is formed in a related insertion type reaction when an N-acetyl-N-nitroso compound is used a diazo precursor; see
- (1981) Journal of the Chemical Society, Chemical Communications , pp. 297
- Chow¹ Polo²

18
- 84912932717
- When the diazoester 3 was decomposed in methanol at room temperature in the presence of rhodium(II) acetate, rhodium(II) trifluoroacetate or rhodium(II) trimethylbenzoate, the ratios of z- to e-alkene obtained were 3.4:1, 3.6:1 and 1.9:1 respectively.

19
- 84912943629
- One such control experiment involved further heating of a 3.6:1 z- to e- mixture of alkenes in methanol in the presence of rhodium(II) trifluoroacetate. After 6 h the ratio of z- to e-alkenes was determined to be 2.2:1; i.e. although there is a slow but detectable double bond isomerisation, it cannot account for the 1:1 mixtures of alkenes that were formed in the original rhodium carbenoid mediated step.

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