02 Son of Stereochemistry worksheet

02 Son of - A with the S-configuration was produced in 68 enantiomeric excess Tetrahedron Lett 2004 45 4481 Cl Tetrahedron Lett 2004 45 3887 HO O H

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CHEMISTRY 225 SON OF STEREOCHEMISTRY WORKSHEET D -Allylglycine, an unusual amino acid, was utilized as the chiral starting material for a synthesis of the antibiotic 2-deoxystreptamine [ Tetrahedron Lett. 2004 , 45 , 3619]. The structure of D - allylglycine is shown below as a Fischer projection. CO 2 H NH 2 CH 2 CH H CH 2 D -allylglycine C CO 2 H CH 2 CH=CH 2 D -allylglycine the enantiomer ? (2) Using the template provided, write a three-dimensional structure for D -allylglycine. ? (2) Using any appropriate stereochemical representation, write a structure for the enantiomer of D -allylglycine ( L -allylglycine). ? (3) Would you expect the p K a of D -allylglycine to be greater than equal to less than the p K a of L -allylglycine? Explain briefly. Consider the structures below. Circle all chiral molecules; underline all achiral molecules. When the following transformation was carried out in the presence of a chiral catalyst, product
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Unformatted text preview: A with the ( S )-configuration was produced in 68% enantiomeric excess [ Tetrahedron Lett . 2004, 45 , 4481]. Cl Tetrahedron Lett. 2004 , 45 , 3887 HO O H 3 C CH 3 Org. Lett. 2004 , 6 , 1535 C C H 3 C Br H CH 3 Br H CH 3 Br Org. Lett. 2004 , 6 , 1531 C O H + OCH 3 O CH 3 OH A (S)-enantiomer ? (2) Rank the substituents at the stereogenic carbon of A in order of descending priorities. > > > ? (2) Write a stereochemical structure for the ( S )-stereoisomer of the product. ? (2) In a related reaction (below) an aromatic aldehyde was converted to hydroxyketone B [ Tetrahedron Lett . 2004, 45 , 4583]. What term best describes the relative configurations of compounds A and B ? CHO O 2 N L-proline OH O CH 3 O 2 N + O B same configuration opposite configuration diastereomeric racemic...
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This note was uploaded on 06/18/2010 for the course CHEM 225 taught by Professor Markdec during the Spring '10 term at University of Michigan-Dearborn.

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02 Son of - A with the S-configuration was produced in 68 enantiomeric excess Tetrahedron Lett 2004 45 4481 Cl Tetrahedron Lett 2004 45 3887 HO O H

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