Organic Letters 2010-01-15

Stereoselective aldol reaction of glutarimides using pseudo C(2) symmetry.

Yohsuke Watanabe, Takashi Yamazaki, Toshio Kubota

Index: Org. Lett. 12(2) , 268-71, (2010)

Full Text: HTML

Abstract

The boron aldol reaction of beta-substituted glutaric imides bearing an oxazolidinone-based auxiliary proceeds with excellent diastereoselectivity; switching the tertiary amine employed between i-Pr(2)EtN or Et(3)N affords enantiomeric lactone product.

Related Compounds

Related Articles:

Comparative characterization of the lactimidomycin and iso-migrastatin biosynthetic machineries revealing unusual features for acyltransferase-less type I polyketide synthases and providing an opportunity to engineer new analogues.

2014-12-16

[Biochemistry 53(49) , 7854-65, (2014)]

Iso-migrastatin congeners from Streptomyces platensis and generation of a glutarimide polyketide library featuring the dorrigocin, lactimidomycin, migrastatin, and NK30424 scaffolds.

2005-08-31

[J. Am. Chem. Soc. 127(34) , 11930-1, (2005)]

Enantiomerization mechanism of thalidomide and the role of water and hydroxide ions.

2012-11-05

[Chemistry 18(45) , 14305-13, (2012)]

Evaluation of new migrastatin and dorrigocin congeners unveils cell migration inhibitors with dramatically improved potency.

2008-11-15

[Bioorg. Med. Chem. Lett. 18(22) , 5951-4, (2008)]

Inhibition of macrophage activation and suppression of graft rejection by DTCM-glutarimide, a novel piperidine derived from the antibiotic 9-methylstreptimidone.

2011-09-01

[Inflamm. Res. 60(9) , 879-88, (2011)]

More Articles...