67826-92-0

Usage

Uses

Used in Chemical Synthesis:
(-)-ISOPINOCAMPHENYLBORANE TMEDA COMPLEX is used as a chiral hydroboration reagent for the asymmetric synthesis of various organic compounds. Its application reason is to facilitate the formation of specific enantiomers, which are crucial in the development of pharmaceuticals and other chiral molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (-)-ISOPINOCAMPHENYLBORANE TMEDA COMPLEX is used as a catalyst for the kinetic resolution of racemic esters and ketones. The application reason is to selectively convert one enantiomer of a racemic mixture into a product, leaving the other enantiomer unreacted. This process is essential for obtaining pure enantiomers, which are often required for the development of effective and safe drugs.
Used in Research and Development:
(-)-ISOPINOCAMPHENYLBORANE TMEDA COMPLEX is also used in research and development for the study of new reaction mechanisms and the development of novel synthetic methods. The application reason is to explore the potential of this complex in various chemical transformations and to expand its utility in the synthesis of complex molecules and materials.

InChI:InChI=1/2C10H19B.C6H16N2/c2*1-6-8-4-7(5-9(6)11)10(8,2)3;1-7(2)5-6-8(3)4/h2*6-9H,4-5,11H2,1-3H3;5-6H2,1-4H3/t2*6-,7-,8+,9-;/m11./s1

Upstream product

• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 7785-26-4 (-)-α-pinene 
• 13292-87-0 dimethylsulfide borane complex 

Downstream Products

• 82248-44-0 ((1S,2S)-2-Phenyl-cyclopentyl)-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane 

Relevant academic research and scientific papers

A Short Synthesis of (+)-Brefeldin C through Enantioselective Radical Hydroalkynylation

A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows a high trans diastereoselectivity to be achieved during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis requires six product purifications and it provides (+)-brefeldin C in 18 % overall yield.

Enantioselective Hydroazidation of Trisubstituted Non-Activated Alkenes

A one-pot procedure for the enantioselective hydroazidation of non-activated trisubstituted alkenes is described. Hydroboration with monoisopinocampheylborane (IpcBH2) provides dialkylboranes that are in situ selectively converted into monoalkyl-substituted catecholboranes; these undergo radical azidation upon treatment with benzenesulfonyl azide and a radical initiator. Enantiomerically enriched azides were thus obtained in yields of 59–81 % and enantioselectivities of up to 94:6 e.r. (98:2 e.r. if the intermediate dialkylborane is purified by crystallization). A rapid access to enantiomerically pure (+)-rodocaine is also described. The use of other arenesulfonyl radical traps enables enantioselective hydroallylation, hydrosulfanylation, and hydrobromination reactions with yields of 71–86 %.