Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 357, Issue 16-17, Pages 3627-3638Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201500550
Keywords
asymmetric catalysis; aza-Diels-Alder reaction; 3-methyl-4-arylpiperidines; trans-perhydroindolic acid
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Funding
- National Natural Science Foundation of China [21232004, 21372152, 21402117, 21450110059]
- Nippon Chemical Industrial Co., Ltd.
- Shanghai Jiao Tong University (SJTU)
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An efficient trans-perhydroindolic acid-catalyzed asymmetric aza-Diels-Alder reaction of cyclic 1-azadienes and propanal was developed for the synthesis of chiral 3-methyl-4-aryldehydropiperidine derivatives (up to 98% yield and 99% ee). Such scaffolds are often found in bioactive compounds and medicines. A gram scale reaction was carried out with a low catalyst loading to give the desired product in high yield and with excellent enantioselectivity. The resulting dehydropiperidine derivatives can be further transformed to chiral 3-methyl-4-aryl-substituted piperidines with high efficiency.
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