Department of Chemistry

Professor Ian Fleming

Ian Fleming's home page

Pembroke College

Telephone: 01223 336372

E-mail: if10000@cam.ac.uk

I am retired from active research, and no longer have graduate students or post-docs.

In a research career from 1959-2002, I was interested in understanding organic reactions, with special emphasis since 1972 on the uses of organosilicon chemistry to solve problems of chemo-, regio- and stereocontrol in organic synthesis. Our early work on organosilicon chemistry1 established that the trimethylsilyl group could be used to control the outcome of carbocation reactions 1 to 22 Later we established how the stereochemistry of open-chain electrophilic attack on a double bond adjacent to a stereogenic centre could be controlled when one of the substituents on the stereogenic centre was a phenyldimethylsilyl group 3, having established that it was easy to introduce, using a silyl-cuprate reagent, and easily converted into a hydroxyl with retention of configuration 4 to 53 These investigations led to new synthetic methods,4 which in turn led to syntheses of several natural products.5

Selected Publications

1. Some Uses of Silicon Compounds in Organic Synthesis, Chem. Soc. Rev., 1981, 10, 83-111.
2. Controlling the Outcome of a Carbocation-initiated Cyclisation, J. Chem. Soc., Perkin Trans. 1, 1984, 1815-1819.
3. The Phenyldimethylsilyl Group as a Masked Hydroxy Group, J. Chem. Soc., Perkin Trans. 1, 1995, 317-337.
4. The Diastereoselectivity of Electrophilic Attack on Trigonal Carbon Adjacent to a Stereogenic Centre, 10 papers: J. Chem. Soc., Perkin Trans. 1, 1992, 3257-3369.
5. Stereocontrol in organic synthesis using silicon-containing compounds, J. Chem. Soc., Perkin Trans. 1, 10 papers: 1998, 2645-2747.