Application of the iron acyl complex R-(-)-[(η5-C5H5)Fe(CO)(PPh3)- COCH2O({{1R,2S}},5Rmenthyl)] as a homochiral formyl anion equivalent

✍ Scribed by Stephen G. Davies; David Middlemiss; Alan Naylor; Martin Wills

• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 307 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)99172-x

✦ Synopsis

Surnmnry: The enantiomerically pure iron acyl complex R-(-)-[($-CSH5)Fe(CO)(PPh3)-CUCH20({lR,2S,5R]menthyl))]

tepresents a source of homochiral formyl anion equivalent applicable to the synthesis of enantiomerkally pare a-hydroxy acetals from aldehydes.

The formyl anion or a synthetic equivalent thereof, has wide application in synthetic organic chemistry.

Although a number of formyl anion synthons have been reported,1 there are relatively few examples of reagents which are designed to add preferentially to only one prochiral face of a carbony group, such as an aldehyde, and thereby provide an asymmetric synthesis of a-hydroxy aldehydes. 2 Such a synthon would represent a source of homochiral formyl anion. In this paper we describe the development of a homochiral formyl anion equivalent based on a homochiral a-alkoxy iron acyl complex.

Deprotonation of racemic a-benzyloxy iron acyl complex 13 gave a deep red solution of the E-enolate 2.