Standard Article

Additions of Allyl, Allenyl, and Propargylstannanes to Aldehydes and Imines

  1. Benjamin W. Gung

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or064.01

Organic Reactions

Organic Reactions

How to Cite

Gung, B. W. 2004. Additions of Allyl, Allenyl, and Propargylstannanes to Aldehydes and Imines. Organic Reactions. 64:1:1–113.

Author Information

  1. Miami University, Oxford, Ohio

Publication History

  1. Published Online: 15 OCT 2004

Abstract

Natural products that contain stereocenters such as those having polyacetate and polypropionate structures are of considerable interest. Current technology for constructing these chiral molecules consists of strategies broadly defined as “acyclic stereocontrol.” The most efficient tools for this strategy include modern aldol reactions and the reaction of carbonyl compounds with allylmetal reagents. In order to achieve highly efficient syntheses of natural products rich with stereochemistry, highly stereoselective transformations are required. One solution is the use of allylstannane reagents. Their advantages include ease of handling, relative stability, and selective reactivity. The addition of allystannanes to aldehydes combines the process of C[BOND]C bond formation with the stereoselective production of one or two new stereocenters. The configuration of these centers is predictable based on reaction conditions. Oxygen substitution also contributes to the versatility of these reagents. Recently developed chiral allenystannanes and the use of InCl3 as a transmetallation agent have greatly enhanced the practical utility of these reagents. This chapter is limited mainly to carbonyl and imine addition reactions, most of which create one or two new stereocenters.

Keywords:

  • allylstannanes;
  • allenylstannanes;
  • propargylstannanes;
  • thermal reactions;
  • promoted reactions;
  • Lewis acid;
  • transmetallation;
  • achiral aldehydes;
  • chiral aldehydes;
  • indium trichloride;
  • scope;
  • limitations;
  • natural products;
  • addition reactions;
  • stannane reagents;
  • boranes;
  • tin chlorides;
  • method comparisons;
  • imines;
  • palladium catalyst;
  • synthesis applications;
  • oxygen substitution