Erythrulose as a multifunctional chiron: Highly stereoselective boron aldol additions

Tetrahedron Letters

Volumn 40, Issue 5, 1999, Pages 1065-1068

  Marco, J Alberto ^a   Carda, Miguel ^b   Falomir, Eva ^b   Palomo, Claudio ^c   Oiarbide, Mikel ^c   Ortiz, J Aurelio ^c   Linden, Anthony ^d  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITAT JAUME I   (Spain)

^c UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^d UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BORON; ERYTHRULOSE 3,4 ACETONIDE; GLYCOLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CHIRON;

EID: 0033613760     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)80113-0     Document Type: Article

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43. 2 solution (3 mL). After stirring for 1 h at room temperature, the mixture was poured into brine and extracted with ether. Solvent removal in vacuo and column chromatography of the residue on silica gel (hexane-EtOAc 9:1 and then 4:1) afforded the aldol addition product 7 as essentially one diastereomer (the minor diastereomers were almost undetectable by NMR of the crude reaction mixture). Chemical yields: R=TES, 7a (85%), 7b (77%), 7c (80%), 7d (87%); R=TBS, 7a (87%), 7b (86%), 7c (83%), 7d (86%), 7e (89%); R=TPS, 7b (85%), 7c (78%).
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57. The computational calculations are being performed by Dr. J. Murga. The experimental results presented here are part of the projected Ph.D. Thesis of E.F. Complete theoretical and experimental data will be published in due course.