Tebbe's reagent

(A) Compounds containing carbonyl groups such as aldehydes, ketones, amides, esters, and thiolactones can be methylenated by using Tebbe's reagent.1 (Chemical Equation Presented) (B) Selective methylenation of aldehydes and ketones in the presence of an ester or amide group can be achieved using Tebbe's reagent.7a This regioselectivity is also found in the methylenation of a methyl ester in the presence of a bulky silyl ester group.7b (Chemical Equation Presented) (C) An easy and effective synthesis of enantiomerically pure β-amino ketones and γ-amino alcohols can be achieved by Tebbe methylenation of proline derivatives. 8 (Chemical Equation Presented) (D) Cyclic enol ether 3 is easily synthesized from olefinic ester 2 by using two equivalents of Tebbe reagent.9 (Chemical Equation Presented) (E) C-glycosides10 can be readily prepared from 3-hydroxyl glycal esters via Tebbe methylenation and subsequent Claisen rearrangement.2 1,6-Linked C-disaccharides can also be prepared by Tebbe's reagent and Claisen rearrangement.3 (Chemical Equation Presented) (F) Since 1,2-cis glycosides are difficult to prepare, Tebbe methylenation with N-iodosuccinimide has been used as intramolecular aglycon delivery to synthesize these.11 (Chemical Equation Presented) (G) Vinyl silanes play an important role as vinyl anion equivalents for stereospecific electrophilic reactions. They can be readily prepared with the help of Tebbe's reagent.4 (Chemical Equation Presented) (H) Allenyl ketene is synthesized from cyclobutenedione by Tebbe methylenation.5 The allenyl tyetene can then undergo different nucleophilic and electrophilic additions and cycloaddition reactions. (Chemical Equation Presented) (I) Sulfoxides, selenoxides, and pyridinium N-oxides can be converted into sulfides, selenides, and 2-methyl pyridines, respectively, on treatment with Tebbe's reagent.12 (Chemical Equation Presented). © Georg Thieme Verlag Stuttgart.