Highly diastereoselective Michael reaction of (S)-mandelic acid enolate. Chiral benzoyl carbanion equivalent through an oxidative decarboxylation of α-hydroxyacids

Tetrahedron Letters

Volumn 43, Issue 47, 2002, Pages 8463-8466

  Blay, Gonzalo ^a   Fernández, Isabel ^a   Monje, Belén ^a   Pedro, José R ^a   Ruiz, Rafael ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLAN 4 ONE; 2 HYDROXYACID; ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; KETONE DERIVATIVE; LITHIUM DERIVATIVE; LITHIUM ENOLATE; MANDELIC ACID; PIVALALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DECARBOXYLATION; DECOMPOSITION; DIASTEREOISOMER; ENANTIOMER; HYDROLYSIS; MICHAEL ADDITION; OXIDATION; STEREOCHEMISTRY;

EID: 0037131745     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02099-3     Document Type: Article

References (24)

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18. The stereochemical structures of the Michael adducts 5 and 6 were elucidated by NOEs. These experiments showed that in all of the cases the electrophile 4 entered anti to the t-Bu group. The absolute stereochemistry of the newly formed quaternary carbon was then assigned to be S upon the consideration that the absolute configuration of the acetal carbon bearing the t-Bu group in 2 is S (see Refs. 5 and 6 ) and it keeps unaltered from 2 to 5 or 6. For the assignment of the stereochemistry at the tertiary stereocenter see Ref. 12.
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21. The stereochemical structures of the cyclic hemiacetal acids 7a, 8a, and 8b, and lactone acids 7c and 8c was established by NOEs. The absolute stereochemistry of the tertiary carbon was assigned upon the consideration that the absolute configuration of the quaternary carbon bearing the carboxy group was S in all the cases as explained in Ref. 9 . These experiments also allowed the complete stereochemistry of compounds 5 and 6 to be established. For example, the new tertiary stereocenter was found to be R in compound 7a, and consequently the same configuration was assigned to this carbon in its precursor 5a.
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23. However, the cyclic compounds 7c and 8c, which have a lactone instead of a hemiacetal moiety, did not react under these conditions.
24. Racemic mixtures of 1,4-dicarbonyl compounds were prepared starting from racemic mandelic acid.