Abstract

Enantioselective reduction of prochiral ketones to their corresponding optically active alcohols is one of the most powerful methodologies utilized in medicinal asymmetric synthesis. We have developed a novel chiral Lewis acid (TarB-X) that is used in combination with LiBH4 for this purpose. The Lewis acid is derived from naturally occurring (L)-tartaric acid providing an inexpensive route to optically pure compounds. Current research is focused extending the use of TarB-X for the enantioselective reduction of other substrates.

Publications:

Kim, Jinsoo; Singaram, Bakthan. Enantioselective reduction of aliphatic ketones using NaBH4 and TarB-NO2, a chiral boronic ester. Abstracts of Papers, 232nd ACS National Meeting, San Francisco, CA, United States, Sept. 10-14, 2006 (2006).

Kim, Jinsoo; Suri, Jeff T.; Cordes, David B.; Singaram, Bakthan. Asymmetric Reductions Involving Borohydrides: A Practical Asymmetric Reduction of Ketones Mediated by (L)-TarB-NO2: A Chiral Lewis Acid. Organic Process Research & Development (2006), 10(5), 949-958.

Cordes, David B.; Kwong, Tracey J.; Morgan, Kellie A.; Singaram, Bakthan. Chiral styrene oxides from a-haloacetophenones using NaBH4 and TarB-NO2, a chiral Lewis acid. Tetrahedron Letters (2006), 47(3), 349.

Cordes, David B.; Nguyen, Thao M.; Kwong, Tracey J.; Suri, Jeff T.; Luibrand, Richard T.; Singaram, Bakthan. Asymmetric reduction of ketones under mild conditions using NaBH4 and TarB-NO2: An efficient and unusual chiral acyloxyborohydride reducing system. European Journal of Organic Chemistry (2005), (24), 5289.

Suri, Jeff T.; Vu, Truong; Hernandez, Arturo; Congdon, Julie; Singaram, Bakthan. Enantioselective reduction of aryl ketones using LiBH4 and TarB-X: a chiral Lewis acid. Tetrahedron Lett. 2002, 43, 3649-3652.