. Author manuscript; available in PMC: 2022 Aug 1.

Published in final edited form as: Org Biomol Chem. 2022 Jun 1;20(21):4314–4319. doi: 10.1039/d2ob00439a

Table 3.

Sequential Oxidation-Aldol Reaction^[a]

entry	Oxidation Catalyst	Aldol Catalyst	Time (h)^[b] Ox/Aldol	Yield (%)^[c] 8
1	(RR,RR)-17	(RR,SS)-12	9/12	80
2^[d]	14	9	9/72	21
3	(RR,RR)-17	(RR,SS)-12	9/72	25
4	(RR,RR)-8	(RR,SS)-12	72/NA	0
5	(RR,RR)-17	(RR,SS)-8	9/72	trace
6	(RR,SS)-17	+ (S,S)-15	9/72	trace
7	(RR,RR)-17	+ (S,S)-15	9/12	81

^[a]

Oxidation: p-nitrobenzalcohol 12 (1.0 mmol), isobutyl alcohol 14 (1.0 mmol), DIB (2.04 mmol) and catalyst (0.2 mmol) followed by aldol reaction.

^[b]

Total reaction time not including catalyst isolation/exchange processes (approx. 30 min).

^[c]

Isolated yield of 8.

^[d]

Pyrrolidine 9 was added upon completion of oxidation by 14.