Chiral 1,3-Cyclobutane Amino Acids: Syntheses and Extended Conformations. -Oxidative cleavage of verbenone (I) produces the keto acid (II) from which both enantiomers (VIII) and (X) of N-protected 1,3-cyclobutane amino acid can be prepared. An analogous sequence starting from Ξ± -pinene (XI) leads t
Chiral 1,3-cyclobutane amino acids: Syntheses and extended conformations
β Scribed by Kevin Burgess; Shiming Li; Joe Rebenspies
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 215 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Optically active samples of the N-protected 1,3-cyclobutane amino acids 1 and 2 were prepared from ct-pinene. The synthesis of 1 is enantiodivergent insofar as both optical antipodes of the product can be prepared from the same a-pinene enantiomer. Single crystal X-ray diffraction studies of derivatives of 1 reveal these compounds can have extended conformations.
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The stereospecific syntheses of cis-and trans-1-amino-3hydroxymethyl-cyclobutane-1-carboxylz acids from 3-oxabicyclo[3.l.llheptan-2-one-1-carboxylic acid are described. (Recebed in UK 6 Jamrary 1988) The three achiral cyclobutane amino acids, cia-1-amino-3-hydroxymethyl-cyclobutane--1-carhoxylic aci
Even a 2.5 month "old' CH2C12 solution of ( 2 4 which had been stored in the refrigerator, underwent a smooth reaction with cyclopentadiene to the adduct (3d}. [S] H. Wamhofi G. Kunz, unpublished results.
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