Parallel synthesis of ureas and carbamates from amines and CO2 under mild conditions

Organic Letters

Volumn 12, Issue 6, 2010, Pages 1340-1343

  Peterson, Scott L ^a   Stucka, Sabrina M ^a   Dinsmore, Christopher J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBAMIC ACID DERIVATIVE; CARBON DIOXIDE; DRUG DERIVATIVE; UREA;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

AMINES; CARBAMATES; CARBON DIOXIDE; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; UREA;

EID: 77949865266     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100259j     Document Type: Article

References (25)

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18. See the Supporting Information for an image of the Bohdan MiniBlock.
19. For a recent review of the Mitsunobu reaction, see: Swamy, K. C. K. ; Kumar, N. N. B.; Balaraman, E.; Kumar, K. V. P. Chem. Rev. 2009, 109, 2551.
20. Contrary to a recent communication (Chaturvedi, D.; Mishra, N.; Mishra, V. Monatsh. Chem. 2008, 139, 267.) where symmetrical tetrasubstituted ureas were reported. When the conditions reported in this report are utilized, neither symmetrical or unsymmetrical tetrasubstitiuted ureas are observed. See the Supporting Information for details.
21. Based upon the observed formation of the bis-alkylamine urea. This product is formed from the alkylamine condensing with the isocyanate generated from, the alkylamine carbamic acid.
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24. Reacting benzylamine and benzyl alcohol under these reaction conditions produced the bis-benzyl urea rather than the carbamate. See the Supporting Information for details.
25. Stereochemistry was assigned on the basis of comparison to a reference compound synthesized by CDI coupling of (R)-5-hexen-2-ol and tetrahydroisoquinoline. See the Supporting Information for details.