By Satoru Masamune
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Extra info for Organic Syntheses: v. 55
16). Fig. 16. Typical reactions of Fischer-type alkylcarbene complexes. 16). Stereoselective aldol-type additions can be realized with the aid of Fischer-type alkylcarbene complexes [214-2161. In these reactions the metallic fragment can either play the role of a ‘bulky carbonyl group’ or stabilize a given conformation of the substrate by chelate formation [2 16,2171. As in carboxylic esters it is possible to substitute alkoxy groups of Fischertype carbene complexes by non-carbon nucleophiles, such as other alcohols [73,214,218], enols , aliphatic amines [43,64,66,220-2241, aniline , imines , or pyrroles .
72%  oc-'co- acetone when addition is complete, otherwise more oxonium salt must be added. The phases are separated and the aqueous phase is extracted with pentane (50-mL portions; until the extract remains colorless). The combined organic extracts are dried over sodium sulfate and concentrated to 75 mL. 6g (92%) of the title compound as yellow crystals, sufficiently pure for most purposes. Analytically pure material (mp 59°C) can be obtained by column chromatography (degassed silica gel/pentane).
1. Reactivity of carbene complexes towards electrophiles (E+) and nucleophiles (Nu-). Today, however, carbene complexes covering a broad range of different reactivities have been prepared. Often it is no longer possible to predict whether a carbene complex will behave as an electrophile or as a nucleophile. Thus, a reactivity-based nomenclature would be difficult to apply consistently. For this reason in this book compounds with a carbon-metal double bond will be called 'carbene complexes' or 'alkylidene complexes', terms not associated with any specific chemical behavior.
Organic Syntheses: v. 55 by Satoru Masamune