期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 26, 期 19, 页码 4236-4241出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201905773
关键词
C-H functionalization; diastereoselectivity; piperidines; regioselectivity; rhodium
资金
- National Science Foundation [CHE 1626172, CHE 1531620, CHE-1700982] Funding Source: Medline
- NIGMS NIH HHS [R01 GM099142] Funding Source: Medline
- NIH HHS [GM099142] Funding Source: Medline
- Elitenetzwerk Bayern (SYNCAT) Funding Source: Medline
Rhodium-catalyzed C-H insertions and cyclopropanations of donor/acceptor carbenes have been used for the synthesis of positional analogues of methylphenidate. The site selectivity is controlled by the catalyst and the amine protecting group. C-H functionalization of N-Boc-piperidine using Rh-2(R-TCPTAD)(4), or N-brosyl-piperidine using Rh-2(R-TPPTTL)(4) generated 2-substitited analogues. In contrast, when N-alpha-oxoarylacetyl-piperidines were used in combination with Rh-2(S-2-Cl-5-BrTPCP)(4), the C-H functionalization produced 4-susbstiuted analogues. Finally, the 3-substituted analogues were prepared indirectly by cyclopropanation of N-Boc-tetrahydropyridine followed by reductive regio- and stereoselective ring-opening of the cyclopropanes.
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