Magnesium-mediated intramolecular reductive coupling: a stereoselective synthesis of C(2)-symmetric 3,4-bis-silyl-substituted adipic acid derivatives.
Chiral C(2)-symmetric 3,4-bis-silyl-substituted adipic acid derivatives have been synthesised by a Mg/trimethylsilyl chloride-mediated intramolecular reductive coupling of symmetrical disiloxanes of beta-silylacrylic acid N-oxazolidinone derivatives. Efficient and short syntheses of enantiomerically pure enantiomers of 2,6-dioxabicyclo[3.3.0]octane-3,7-dione have been achieved from the bis-silylated adipic acid derivatives using Fleming-Tamao oxidation as the key step.
Kundu
Pintu K
PK
Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai, India.
Ghosh
Sunil K
SK
D000272:Adipates / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D008274:Magnesium / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry; D010084:Oxidation-Reduction; D012821:Silanes / Q000138:chemical synthesis; D013237:Stereoisomerism
D000272:Adipates; D012821:Silanes; C059468:disiloxane; C029900:adipic acid; D008274:Magnesium; D000432:Methanol