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Diastereoselective ...
Diastereoselective Synthesis of N-Methylspiroindolines by Intramolecular Mizoroki–Heck Annulations
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- Lindman, Jens (author)
- Uppsala universitet,Institutionen för läkemedelskemi
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- Gopalan, Greeshma (author)
- Uppsala universitet,Institutionen för läkemedelskemi
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- Palo-Nieto, Carlos, 1985- (author)
- Uppsala universitet,Institutionen för läkemedelskemi
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- Brandt, Peter (author)
- Uppsala universitet,Institutionen för läkemedelskemi
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- Gising, Johan, 1981- (author)
- Uppsala universitet,Institutionen för läkemedelskemi
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- Larhed, Mats (author)
- Uppsala universitet,Institutionen för läkemedelskemi
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(creator_code:org_t)
- 2022-08-26
- 2022
- English.
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In: ACS Omega. - : American Chemical Society (ACS). - 2470-1343. ; 7:36
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Abstract
Subject headings
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- Spiroindolines represent a privileged structure in medicinal chemistry, although stereocontrol around the spirocarbon can be a synthetic challenge. Here we present a palladium(0)-catalyzed intramolecular Mizoroki–Heck annulation reaction from (+)-Vince lactam-derived cyclopentenyl-tethered 2-bromo-N-methylanilines for the formation of N-methylspiroindolines. A series of 14 N-methylspiroindolines were synthesized in 59–81% yield with diastereoselectivity >98%, which was rationalized by density functional theory calculations and confirmed through X-ray crystallography. One spiroindoline was converted to an N- and C-terminal protected rigidified unnatural amino acid, which could be orthogonally deprotected.
Subject headings
- MEDICIN OCH HÄLSOVETENSKAP -- Medicinska och farmaceutiska grundvetenskaper -- Läkemedelskemi (hsv//swe)
- MEDICAL AND HEALTH SCIENCES -- Basic Medicine -- Medicinal Chemistry (hsv//eng)
- NATURVETENSKAP -- Fysik (hsv//swe)
- NATURAL SCIENCES -- Physical Sciences (hsv//eng)
Keyword
- Medicinal Chemistry
- Läkemedelskemi
Publication and Content Type
- ref (subject category)
- art (subject category)
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