Synthesis via organoboranes

H. C. Brown (1975). Organic Synthesis via Organoboranes. New York Wiley. 

One case study within the framework of this project is thus to test the concept of a micro structured reactor plant by applying the fast reaction of the enantioselective synthesis via organoboranes yielding chiral-substituted alcohols. This is typically a batch process carried out in the laboratory using conventional glassware and in the present case has been converted into a continuous process carried out by micro structured devices. This set-up has been used to characterize the physical properties of the backbone system. 

Brown, H. C., Chandrasekharan, J., Ramachandran, P. V. Chiral synthesis via organoboranes. 14. Selective reductions. 41. Diisopinocampheylchloroborane, an exceptionally efficient chiral reducing agent. J. Am. Chem. Soc. 1988,110,1539-1546. 

Brown, H. C., Bhat, K. S., Jadhav, P. K. Chiral synthesis via organoboranes. Part 32. Synthesis of B-(cycloalk-2-enyl)diisopinocampheylboranes of high enantiomeric purity via the asymmetric hydroboration of cycloalka-1,3-dienes. Successful asymmetric allylborations of aldehydes with B-(cycloalk-2-enyl)diisopinocampheylboranes. J. Chem. Soc., Perkin Trans. 1 1991, 2633-2638. 

Racherla, U. S., Brown, H. C, Chiral synthesis via organoboranes. 27. Remarkably rapid and exceptionally enantioselective (approaching 100% ee) allylboration of representative aldehydes at -100 °C under new, salt-free conditions. J. Org. Chem. 1991, 56, 401-404. 

Jadhav PK, Bhat KS, Perumal PT, Brown HC (1986) Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excess. J Org Chem 51 432-439... 

Brown HC, Bhat, KS, RandadRSJ (1989) Chiral Synthesis via Organoboranes. 21. Allyl- and Crotylboration of a-Chiral Aldehydes with Diisopinocampheylboron as the Chiral Auxiliary. 

Brown, H. C. Prasad, J. V. R. V. 1986. Chiral synthesis via organoboranes. 9. crystalline Chelates from borinic and boronic esters. A simple procedure for upgrading borinates and boronates to materials approaching 100% optical purity. 7. Org. Chem. 51 4526-4530. 

Brown HC, Bhat KS. Chiral synthesis via organoboranes. 7. Diastereoselective and enantioselective synthesis of erythro- and threo-p-methylhomoallyl alcohols via enantiomeric (Z)- and (E)-crotylboranes. J. Am. Chem. Soc. 1986 108 5919-5923. 

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