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3. One of the first reported cases involving a Noyori catalyst doing asymmetric hydrogenation of
unfunctionalized ketones is shown below.
trans-RuCl(S)-BINAPI(S, S-DPEN)] cat.
KOBU
OH
Me
Me
nPrOH, H2 (500 psi)
NH2
PPha
PPha
"NH2
(S)-BINAP
(SS)-DPEN
(a) The use of n-propanol solvent under basic conditions was found to be critical for converting the
pre-catalyst shown into an active catalyst. Propose how the pre-catalyst converts to the active
catalyst. Please name each elementary step (e. g. oxidative addition, migratory insertion,
dissociation, etc.).
(b) If D2 were used in place of H2, what would happen to the rate of reaction? Also, do you expect
the product to be singly or doubly deuterated? Explain your answers.
(c) What would happen if the -NH2 groups in (S, S)-DPEN were replaced with -NMe2 groups?
Explain your answer.
(d) Use a quadrant diagram to rationalize the absolute stereochemistry observed in the product. (This
can be difficult, but do your best!)