02 Son of Stereochemistry worksheet key

02 Son of Stereochemistry worksheet key - CHEMISTRY 225 -...

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Unformatted text preview: CHEMISTRY 225 - SON OF STEREOCHEMISTRY WORKSHEET K «8.7 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. CozH 004/14 COzH ’ ' NH I4 1-2 1+ H+ 2 R / \CH2CH=CH2 ” CH2CH=CH2 o—allylglycine N l 2” OllzC/Hfifl‘la o—allylglycine the enantiomer o (2) Using the template provided, write a three-dimensional structure for D-aliylglycine. o (2) Using any appropriate stereochemical representation, write a structure for the enantiomer of D-ally] glycine (L-allyl glycine). o (3) Would you expect the pKa of D-allylglycine to be greater than less than the pKa of L-allylgiycine? Explain briefly. Emu—amqhflwivfi CA“ Oct La ell/Hispawl:o‘i-€J L7 4 (‘Lwal lib). ‘TLQ'IV FWFP‘L Lv(€—\7 nave.- iltlfi’vaLxfia,‘ Vwcl‘i-v exude archival kyl.‘ TL; aLIlil; lo (‘IQHQLH ea Paulo“ (wears-rung} la»? '19 wool awn-mull on. ch‘li "lea-l Consider the structures below. Circle all chiral molecules; underline all achiral molecules. 2004, 45, 3887 ' CH3 \/\R//l./\K/i‘,h///’Z§§m-/ Org. Left. 2004, 6, 1531 When the following transformation was carried out in the presence of a chiral catalyst, product A with the (S)-configuration was produced in 68% enantiomeric excess [Tetrahecb‘on Left. 2004, 45, 4481]. ~enantiomer - (2) Rank the sub stituents at the stereo genic tg‘bon of A in order of descending priorities. , u \ __0H > ./\J >§Cflz€C§> H o (2) Write a stereoohemical structure for the (S)- stereoisomer of the product. 0 (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? OH O r— 0 ha _ r /r- \ 02N——-\ Jun-coo + Jo“ 9F9."l‘?._,. T CH3 02hr k/fl, B same configuration t 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 Stereochemistry worksheet key - CHEMISTRY 225 -...

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