91055-81-1

Upstream product

• 100-50-5 3-Cyclohexene-1-carboxaldehyde 
• 1730-25-2 allylmagnesium bromide 
• 106-95-6 allyl bromide 
• 132653-29-3 α-(2-bromopropen-2-yl)-3-cyclohexen-1-methanol 
• 6493-77-2 methyl cyclohex-3-ene-1-carboxylate 
• 762-72-1 allyl-trimethyl-silane 
• 107-18-6 allyl alcohol 

Downstream Products

• 103385-60-0 1-cyclohex-3-enyl-but-3-en-1-one 

Relevant academic research and scientific papers

Stereoselective Barbier-Type Allylations and Propargylations Mediated by CpTiCl3

CpTiCl2, prepared in situ by manganese reduction of CpTiCl3, is an excellent new system for the Barbier-type allylation and propargylation of carbonyl compounds. It can be used in catalytic amounts when combined with Et3N·HBr/TMSBr, which acts as a regenerating system. The high regio- and stereoselectivity shown by this system makes it useful for prenylation and crotylation processes in the synthesis of natural products.

Oxime-mediated oxychlorination and oxybromination of unactivated olefins

An oxime-mediated oxychlorination and oxybromination of unactivated olefins relying on palladium catalysis has been developed. A wide range of chlorinated and brominated isoxazolines has been synthesized in moderate to good yields. To demonstrate the value of the method, the brominated isoxazoline has been further converted to other useful synthetic feedstock.

Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin

A palladium-catalyzed efficient synthesis of 5-methylisoxazoles via oxime-mediated functionalization of unactivated olefins is described. The reaction affords a variety of 5-methylisoxazoles in moderate to good yields. To further demonstrate the utility of the method, the rapid synthesis of valdecoxib and oxacillin is reported. (Chemical Equation Presented).

Indium triiodide catalyzed direct hydroallylation of esters

The InI3-catalyzed hydroallylation of esters by using hydroand allysilanes under mild conditions has been accomplished. Many significant groups such as alkenyl, alkynyl, cyano, and nitro ones survive under these conditions. This reaction system, provided routes to both homoallylic alcohols and ethers, in which either elimination of the alkoxy moiety or of the carbonyl oxygen atom could be freely selected by changing the substituents on the alkoxy moiety and on the hydrosilane. In addition, the hydroallylation of lactones took place without ring cleavage to produce the desired cyclic ethers in high yields.

Pd-catalyzed nucleophilic allylic alkylation of aliphatic aldehydes by the use of allyl alcohols

Under catalysis of Pd(OAc)2-(P-n-Bu)3, Et 2Zn promotes a variety of allyl alcohols to undergo nucleophilic allylation of aliphatic aldehydes and ketones at room temperature and provides homoallyl alcohols in 60-90 and ca. 60% isolated yield, respectively. The reaction is irreversible and kinetically controlled, and unique regio- and stereoselectivities observed for the allylation with unsymmetrically substituted allyl alcohols are discussed.

APPROACHES TO BICYCLIC RING SYSTEMS VIA 1,5 ALLYLIC ABSTRACTION CYCLISATION

A new 1,5 allylic abstraction, cyclisation sequence has been developed and applied to the synthesis of fused bicyclic systems.Initial studies directed towards the synthesis of the bicyclooctane skeleton are described: vinyl bromide 4 was subjected

1,5 Allylic abstraction, cyclisation: A new route to five membered carbocycles

A new 1,5 allylic abstraction cyclisation sequence has been developed. The method is based upon a novel radical rearrangement and is applicable to the construction of highly functionalised cyclopentanoid ring systems.