Corey’s reagent

Review,1 This review covers synthetic uses of Corey s reagent from January 1974 to December 1985 (345 references). 

Other oxidation procedures were used, e.g., pyridinium chlorochromate (Corey s reagent), and dipyridine Cr(VI) oxide (Collins ... 

These authors also described a three-step synthesis of 13Z-retinoic acid [56], The obtained hydroxydihydropyrane (66%) was oxidized either by Jones s reagent (CrC>3, water, H2SO4, 90%) or Corey s reagent (pyridinium chlorochromate (PCC), 65%). Finally, the dihydropyranone was transformed into retinoic acid (as a mixture of 9E, 13Z, and 9Z,13Z), by /BuOK, according to a known procedure [57], Fig. (26). 

Dimethylsulfoxonium methylide (DMSY, also referred to as Corey s reagent) is a convenient methylene transfer reagent. It appears to be the most used sulfur ylide and a Tetrahedron Report [455] covers most of its chemistry (345 references). In contrast to dimethylsulfonium methylide, which must be used as soon as it is formed, DMSY is much more stable and can be stored for several days at room temperature. It is the reagent of choice in many instances. However, with a,(3-unsaturated ketones the two reagents react in different ways, as shown for cyclohexenone. 

The treatment of methoxymethoxy derivatives 105 and 107 with Me-jSil gave perhydropyrido[l,2-c][l,3]oxazin-l-ones 106 and 108, respectively (06OBC1587). Better yields could be achieved when alcohol 109 was treated either with McySil or with Corey s reagent PrSLi, prepared from PrSH and BuLi. 

A new synthesis of the hydroazulenone (119) has been reported, from the bicyclic dione (116) (Scheme 6)." Initial conversion of (116) into the spiro-oxiran (117) by Corey s reagent (Mc2S—CH2) is followed by BF3-Et20-catalysed rearrangement via the carbo-cation (118) to the azulene derivative (119). 

As an alternative to Corey s reagent, methylene dibromide in the presence of Li may be used to convert aldehydes and ketones to epoxides in 35-90% yield. ... 

Cl Cl" ( = 0 or 1) have been used to convert the tricyclic vic-diol (24) into an o -hydroxy-ketone. Most inorganic oxidants would have caused C—C bond cleavage, giving dicarbonyl compounds, in this situation. The polymer version (25) of Corey s reagent has been recommended for the high-yield oxidation of... 

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