- 4-Isocyanopermethylbutane-1,1,3-triol (IPB): A convertible isonitrile for multicomponent reactions
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The synthesis and applications of 4-isocyanopermethylbutane-1,1,3-triol (IPB) as a new convertible isonitrile (isocyanide) for isocyanide-based multicomponent reactions (IMCRs) like Ugi, Ugi-Smiles, and Passerini reactions are described. The primary products obtained from these IMCRs can be converted into highly activated N-acylpyrroles, which upon treatment with nucleophiles can be transformed into carboxylic acids, esters, amides, alcohols, and olefins. In this sense the reagent can be seen as a neutral carbanion equivalent to formate (HO2C-), and carboxylates or carboxamides etc. (RNu-CO-).
- Neves Filho, Ricardo A.W.,Stark, Sebastian,Morejon, Micjel C.,Westermann, Bernhard,Wessjohann, Ludger A.
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supporting information
p. 5360 - 5363
(2012/10/30)
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- Camphor-based Schiff base ligand SBAIB: An enantioselective catalyst for addition of phenylacetylene to aldehydes
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A series of Schiff base ligands were synthesized from (1R)-camphor. Under the optimal conditions, (+)-SBAIB-a, 10 was found to be an excellent catalyst for the enantioselective addition of phenylacetylene to various aldehydes without utilizing either achiral additives or Ti(OiPr)4. This approach yielded (R)-propargylic alcohols in extremely high yields (up to 99%) and excellent enantioselectivities (up to 92%). The corresponding (S)-propargylic alcohols were synthesized in good to high enantioselectivities (up to 91%) and excellent yields (up to 99%) using (-)-SBAIB-a, 41.
- Boobalan, Ramalingam,Chen, Chinpiao,Lee, Gene-Hsian
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p. 1625 - 1638
(2012/03/22)
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- An efficient catalytic stereoselective route to a key intermediate for the synthesis of the long-lived PGI2 analog ZK 96480 (Cicaprost(TM))
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An expeditious and stereoselective synthesis of a key chiral intermediate (2) for the synthesis of the therapeutically useful PGI2 analog Cicaprost(TM) is described.
- Corey,Helal, Christopher J.
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p. 7511 - 7514
(2007/10/03)
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- Tin-copper transmetalation: Cross-coupling of α-heteroatom-substituted alkyltributylstannanes with organohalides
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Copper(I), in the absence of other transition metals, catalyzes the cross-coupling of (α-(acyloxy)benzyl)-tributylstannanes with allylic bromides in THF in fair to good yields and with aryl/vinyl halides less efficiently or not at all. Simple (α-(acyloxy)
- Falck,Bhatt, Rama K.,Ye, Jianhua
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p. 5973 - 5979
(2007/10/02)
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