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040040

040040-1g



(R)-(+)-t-Butylsulfinamide


CAS Number: 196929-78-9
   
Molecular Formula: C4H11NOS
   
Molecular Weight: 121.20
   
MDL Number: MFCD05861479


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040040-1g
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040040-5g
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040040-25g
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040040-100g
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Purity:98%
 
Pictograms:
Signal Word:Warning
Hazard Statements:H302, H315, H319, H335
Precautionary Statements:P261, P305 + P351 + P338
SDS: See MSDS
 

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Also known as (R)-(+)-2-Methyl-2-propanesulfinamide. A chiral ammonia equivalent for extensive use both in academics and industry.  Readily transformed into P,N-sulfinyl imine ligands through condensation with aldehydes and ketones, which can undergo iridium-catalyzed asymmetric hydrogenation of olefins.1 Useful reagent for preparation of ß-chloro sulfinamides in a synthesis of chiral azridines,2 preparation of  an organocatalyst for enantioselective reduction of imines,synthesis of chiral amines,4,5,6  synthesis of 1,2-amino alcohols,7 cocatalysis of  enantioselective protonation of enol silanes with achiral sulfonic acid,8 and synthesis of (R)-(+)-Salsolidine (I) of high enantiomeric purity using the Pomeranz-Fritsch-Bobbitt methodol.9
 
References:

1.        Org. Lett. 20046, 1800.
2.        Org. Lett. 20068, 3129.
3.        Org. Lett. 20068, 5913.
4.        Tetrahedron 201066, 8933.
5.        Org. Lett. 20046, 1645.
6.        Acc. Chem. Res. 200235, 984.
7.        Tetrahedron Lett. 200142, 2051.
8.        Org. Lett. 201113, 4260.
9.        Tetrahedron: Asymmetry 200718, 557.


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