Skip to main content
. Author manuscript; available in PMC: 2010 Mar 4.
Published in final edited form as: Tetrahedron Lett. 2009 Mar 4;50(9):995–998. doi: 10.1016/j.tetlet.2008.12.061

Table 3.

Reduction of representative chiral ketones using 1%mol of aminoborate ester 1.a

Entry Substrate Yield (%)b Ee (%)c Config.d14
1e graphic file with name nihms83681t1.jpg 93 95 (R)
2 graphic file with name nihms83681t2.jpg 91 96 (R)
3 graphic file with name nihms83681t3.jpg 90 96 (R)
4 graphic file with name nihms83681t4.jpg 92 99 (R)
5 graphic file with name nihms83681t5.jpg 95 99 (R)
6 graphic file with name nihms83681t6.jpg 88 98 (S)
7 graphic file with name nihms83681t7.jpg 94 99 (R)
a

The reduction was carried out using 0.7 equivalent of borane-DMS in THF at room temperature.

b

Isolated yield after distillation in a Kugelrohr apparatus.

c

Determined by GC of acetate on chiral column.

d

Absolute configuration was determined by comparison of optical rotations with literature values. The configuration of new optical active compounds was assigned by analogy.

e

The reduction was carried out using 1.7 equivalent of borane-DMS.