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Relevant articles and documentsAll total 1 Articles be found

Regio- and stereoselective synthesis of the enantiomers of monoterpene-based β-amino acid derivatives

Szakonyi, Zsolt,Martinek, Tamas A.,Sillanpaeae, Reijo,Fueloep, Ferenc

, p. 2442 - 2447 (2008/03/13)

The regio- and stereospecific addition of chlorosulfonyl isocyanate to cis-δ-pinene enantiomers has furnished monoterpene-fused β-lactams. The observed regioselectivity can be explained by ab initio DFT modeling of transition state structures. In contrast with the less reactive α-pinane-fused β-lactam 4, the resulting β-lactams 5 and 13 containing an amino group connected to a secondary carbon possess similar reactivity to the cycloalkane-fused analogues and can be easily converted to the β-amino acid and its protected derivatives. The base-catalyzed isomerization of the cis-amino ester afforded the corresponding trans-amino ester in moderate yield.

Process route upstream and downstream products

Process route



(1R,2R,3S,4R,5R)-2-tert-butoxycarbonylamino-4,6,6-trimethylbicyclo[3.1.1]heptane-3-carboxylic acid

(1R,2R,3S,4R,5R)-2-tert-butoxycarbonylamino-4,6,6-trimethylbicyclo[3.1.1]heptane-3-carboxylic acid

Conditions Yield
With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 7h;
(1R,2R,3S,4R,5R)-2-amino-4,6,6-trimethylbicyclo[3.1.1]heptane-3-carboxylic acid hydrochloride

(1R,2R,3S,4R,5R)-2-amino-4,6,6-trimethylbicyclo[3.1.1]heptane-3-carboxylic acid hydrochloride

di-<i>tert</i>-butyl dicarbonate

di-tert-butyl dicarbonate

(1R,2R,3S,4R,5R)-2-tert-butoxycarbonylamino-4,6,6-trimethylbicyclo[3.1.1]heptane-3-carboxylic acid

(1R,2R,3S,4R,5R)-2-tert-butoxycarbonylamino-4,6,6-trimethylbicyclo[3.1.1]heptane-3-carboxylic acid

Conditions Yield
With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 6h; pH=8;

1000304-38-0 Upstream products

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  • BOC Sciences
  • Business Type:Trading Company
  • Contact Tel:1-631-485-4226
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  • Main Products:41
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