Diastereoselective Baylis-Hillman reaction: Use of sugar derived aldehydes as chiral electrophiles

Synlett

Volumn , Issue 6, 2003, Pages 888-890

  Radha Krishna, Palakodety ^a   Kannan, Vembaiyan ^a   Sharma, Gangavaram V M ^a   Ramana Rao, Mallem H V ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Activated alkene; Baylis Hillman reaction; Chiral electrophiles; Sugar derived aldehydes; Tertiary amine

Indexed keywords

ALDEHYDE; ALKENE; AMINE; CARBOHYDRATE;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; COVALENT BOND; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0038522867     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

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21. The energy minimization was carried out using Sybyl 6.8 with default Tripose force field Parameters. Minimization was done first with steepest discent followed by conjugate gradient methods for a maximum of 2000 iteration each or RMS deviation of 0.005 kcal/mole which ever was earlier.
22. 4) and concentrated under reduced pressure to get a residue, which was purified by chromatography (Si-gel 60-120 mesh, EtOAc:hexane, 1:9) to afford adducts 1a-c, 2a-c, 3a and 3c in 56-82% yield.
23. 6: C, 59.98, H, 8.05; found: C, 59.93, H, 8.12.