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Relevant academic research and scientific papers

ORGANOBORANES-34; GENERAL SYNTHESIS OF CHIRAL BORONIC AND BORINIC ESTERS VIA ASYMMETRIC HYDROBORATION-DISPLACEMENT. CARBENOIDATION OF CHIRAL BORINIC ESTERS TO ACYCLIC KETONES OF HIGH ENANTIMERIC PURITIES

Asymmetric hydroboration of appropriate alkenes with diisopinocampheylborane (Ipc2BH) or monoisocampheylborane (IpcBH2) produces intermediates that readily eliminate α-pinene on treatment with acetaldehyde, providing a direct, convenient route to chiral boronic esters of high enantiomeric purities.Mixed chiral trialkylboranes, readily prepared by stepwise hydroboration of appropriate alkenes with IpcBH2, eliminate α-pinene on treatment with acetaldehyde under very mild conditions.The procedure makes readily available chiral borinic esters of high enantiomeric purities.The synthetic utility of chiral borinic esters is demonstrated by converting them into acyclic ketones including an alarm pheromone of the ant Manica mutica.

Hydroboration. 87. Controlled and Sequential Hydroboration of Simple Representative Alkenes with Methylborane in Tetrahydrofuran. An Examination of the Directive Effects in the First and Second Stages of Hydroboration

Methylborane (MeBH2), the simplest of the monoalkylboranes, possesses extraordinary hydroborating characteristics in tetrahydrofuran.In this solvent MeBH2 selectively hydroborates all important classes of alkenes, hindered and nonhindered, to yield the methylalkylboranes MeRBH.These dialkylboranes are readily converted into and isolated as their borinic esters, MeRBOR', which in turn can be transformed into methyl ketones, thus providing a simple and highly regio- and stereoselective synthesis of the latter.The addition of a second equivalent of another alkene to the methylalkylborane gives a sequential hydroboration product, MeRARBB.This mixed trialkylborane is readily converted into the corresponding tertiary alcohol via carbonylation-oxidation.The ability to hydroborate an alkene in consecutive stages enables the regioselectivity of the first and second stages of hydroboration to be determined.Thus, the first hydroboration of 1-hexene gives a C-1/C-2 ratio of 98.5:1.5, similar to values obtained with 9-BBN and Sia2BH.The second hydroboration of cis-4-methyl-2-pentene occurs with complete regioselectivity, i.e., 100:0, surpassing the values obtained with the two aforementioned hydroborating agents.MeBH2 is the first example of a sterically nonhindered monoalkylborane capable of stepwise hydroborations of all classes of alkenes.

Electrochemical Coupling of Activated Olefins and Alkyl Dihalides: Formation of Cyclic Compounds

The electrochemical coupling of dimethyl maleate, methyl cinnamate, 4-phenyl-3-buten-2-one, or methyl acrylate with dibromomethane, 1,3-dibromopropane, 1,4-dibromobutane or other substituted alkyl dihalogenides gave satisfactory yields of cyclic products.The reactions were performed in an undivided cell fitted with a sacrificial aluminum anode, in N-methylpyrrolidone (NMP), at constant current, and at room temperature.The role of the anodically generated metallic ions in this cyclocondensation has been evidenced.

METHYLBORANE - A REMARKABLE UNHINDERED MONOALKYLBORANE WHICH ACHIEVES THE CONTROLLED SEQUENTIAL HYDROBORATION OF REPRESENTATIVE ALKENES

Methylborane, MeBH2, the simplest of the monoalkylboranes, possesses extraordinary hydroboration characteristics in tetrahydrofuran.In this solvent, methylborane is capable of monohydroborating the usual classes of alkenes, hindered and unhindered, to provide the simple alkylmethylboranes, RMeBH.The addition of a second equivalent of another alkene to the alkylmethylborane formed initially produces the sequential hydroboration product, RR'MeB.In all cases there is no evidence of redistributed products.