Synthesis of a new enantiomerically pure constrained homoserine

Avenoza, Alberto; Cativiela, Carlos; Fernández-Recio, Miguel A.; Peregrina, Jesús M.

doi:10.1016/0957-4166(96)00067-5

Cited by 34 publications

(5 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The data reported in the literature for the cycloaddition reactions of cyclopentadiene with (−)-menthyl esters of unsubstituted aminoacrylates showed that the H-1 and H-4 configurations of the norbornene ring are opposite in the exo and endo series for the major isomers, but for H-2, the same configuration holds. Furthermore, the crowded side of the olefin in compounds 12b , c corresponds to the chiral acrylates of the literature.…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Synthesis of 2-Amino-3-hydroxynorbornene-2-carboxylic Acid Derivatives

et al. 2001

View full text Add to dashboard Cite

The enantioselective synthesis of 2-amino-3-hydroxynorbornene-2-carboxylic acid derivatives (5) was studied using the Diels-Alder reaction between cyclopentadiene and different dienophiles, i.e., alkyl 5-oxo-2-phenyloxazol-4-methylenecarbonates (1) or 2-benzoylamino-3-alkoxycarbonyloxy-acrylates (12), operating with different Lewis acids and both with thermal and with ultrasound conditions. The enantioselective synthesis of the exo/endo compounds 5c,d and 5'c,d was achieved starting from the chiral menthyl acrylates 12b,c using Mg(ClO(4))(2) as the catalyst and ultrasound. The cycloadducts were obtained in very good yield, in mild conditions, in short time, and in good diastereomeric excess (exo, 80%; endo, 87%). Finally, the use of alkylidene-oxazolones or acrylates and EtAlCl(2) or Mg(ClO(4))(2) as the catalyst allowed control of the cycloaddition reaction in favor of the exo or endo products.

show abstract

Section: Resultsmentioning

confidence: 99%

Asymmetric Synthesis of 2-Amino-3-hydroxynorbornene-2-carboxylic Acid Derivatives

et al. 2001

View full text Add to dashboard Cite

show abstract

“…Often free-radical reductions with tributyltin hydride are used to remove a functional group that has been incorporated in an amino acid derivative as part of an overall synthetic strategy. Accordingly, reactions of the derivatives of nitrovaline 207 and nitroleucine 208 were used to substitute the nitro group for hydrogen, in syntheses of amino acid derivatives using alkyl nitronates. , Xanthate transfer cyclizations and addition reactions have been used in the synthesis of amino acid derivatives, as discussed in more detail below, and reductive cleavage of the product xanthates has been exploited to increase the utility of these processes. , Iodides have been reduced with tributyltin hydride, as part of syntheses of constrained hydroxy amino acid derivatives, − while tris(trimethylsilyl)silane has been exploited in a similar manner for the synthesis of bicyclic amino acid derivatives …”

Section: Functional Group Transformationsmentioning

confidence: 99%

“…68,129 Xanthate transfer cyclizations and addition reactions have been used in the synthesis of amino acid derivatives, as discussed in more detail below, and reductive cleavage of the product xanthates has been exploited to increase the utility of these processes. 218,219 Iodides have been reduced with tributyltin hydride, as part of syntheses of constrained hydroxy amino acid derivatives, [220][221][222] while tris(trimethylsilyl)silane has been exploited in a similar manner for the synthesis of bicyclic amino acid derivatives. 223 Barton esters of aspartate and glutamate derivatives have been used to remove side-chain carboxyl groups.…”

Section: Functional Group Transformationsmentioning

confidence: 99%

Free-Radical Reactions in the Synthesis of α-Amino Acids and Derivatives

1997

View full text Add to dashboard Cite

“…The key reaction for their preparation was the Diels−Alder reaction using different dienes and, as dienophiles, 1-aminoacrylate derivatives or 4-arylidene-5(4 H )-oxazolones, , the latter being masked amino acids. Final products were obtained by reduction of the cyclohexene ring.…”

Section: Introductionmentioning

confidence: 99%

A Highly Diastereoselective Approach to Conformationally Constrained Serine Analogues: Synthesis of an α-Amino-β-hydroxycyclohexenecarboxylic Acid and Derivatives

1999

View full text Add to dashboard Cite

A diastereospecific synthesis of α-amino-β-hydroxycyclohexenecarboxylic acid (7) was found starting from 4-chloromethylene-5(4H)-oxazolone (1) which reacted with 2,3-dimethylbutadiene in the presence of EtAlCl2. The Diels−Alder reaction gave two diastereoisomeric cycloadducts 2 and 3, depending on the configuration of the starting dienophile 1. Compounds 2a and 3 were transformed into the ester 4 and the oxazoline 6, respectively, by reaction with MeOH and p-TSA. The reaction of 2a and 3 with dimethylamine in ethanol solution gave the corresponding amides 8 and 9, respectively, which were transformed into the bicyclic oxazoline 10 on reaction with Na2CO3 in acetonitrile. On acidic hydrolysis both oxazolines 6 and 10 were transformed into α-amino-β-hydroxycyclohexenecarboxylic acid (7) that includes the serine skeleton.

show abstract

Synthesis of a new enantiomerically pure constrained homoserine

Cited by 34 publications

References 23 publications

Asymmetric Synthesis of 2-Amino-3-hydroxynorbornene-2-carboxylic Acid Derivatives

Asymmetric Synthesis of 2-Amino-3-hydroxynorbornene-2-carboxylic Acid Derivatives

Free-Radical Reactions in the Synthesis of α-Amino Acids and Derivatives

A Highly Diastereoselective Approach to Conformationally Constrained Serine Analogues: Synthesis of an α-Amino-β-hydroxycyclohexenecarboxylic Acid and Derivatives

Contact Info

Product

Resources

About