Stereodivergent catalytic doubly diastereoselective nitroaldol reactions using heterobimetallic complexes

Org Lett. 2008 Jun 5;10(11):2231-4. doi: 10.1021/ol800653d. Epub 2008 May 9.

Abstract

Stereodivergent construction of three contiguous stereocenters in catalytic doubly diastereoselective nitroaldol reactions of alpha-chiral aldehydes with nitroacetaldehyde dimethyl acetal using two types of heterobimetallic catalysts is described. A La-Li-BINOL (LLB) catalyst afforded anti,syn-nitroaldol products in >20:1-14:1 selectivity, and a Pd/La/Schiff base catalyst afforded complimentary syn,syn-nitroaldol products in 10:1-5:1 selectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Lanthanum / chemistry*
  • Lithium / chemistry*
  • Nitrogen / chemistry*
  • Organometallic Compounds / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Aldehydes
  • Organometallic Compounds
  • Lanthanum
  • Lithium
  • Nitrogen