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497401 Aldrich

(R)-(+)-2-Methyl-2-propanesulfinamide

98%

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Auxiliaries, Sulfur-Based
InChI Key   CESUXLKAADQNTB-SSDOTTSWSA-N
assay   98%
optical activity   [α]20/D +4°, c = 1.0242 in chloroform stab. with amylenes
mp   103-107 °C(lit.)
storage temp.   2-8°C

Description

Packaging

1, 5, 25 g in poly bottle

Application

(R)-(+)-2-Methyl-2-propanesulfinamide may be used to prepare N-(1-cyclohexylmethylidene)-2-methylpropane-2-sulfinamide via copper mediated condensation with cyclohexane carboxaldehyde. It may also be used to prepare (20E)-N-[t-butyl-(R)-sulfinyl]-3β-(t-butyldimethylsilyloxy)-pregn-5-en-20-imine, an intermediate for the development of androgen receptor antagonists.

Ellman′s Sulfinamides

Can be readily transformed into P,N-sulfinyl imine ligands through condensation with aldehydes and ketones, which can undergo iridium-catalyzed asymmetric hydrogenation of olefins.

Preparation of ß-chloro sulfinamides in a synthesis of chiral azridines. Also used to prepare an organocatalyst for enantioselective reduction of imines.

Useful reagent for synthesizing chiral amines.

Price and Availability

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Ellman Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Ellman Group – Professor Product Portal
Keywords: Arylations, Asymmetric synthesis, C-C bond formation, Catalysis, Drug discovery, Ligands, Pharmaceutical

S-Chirogenic Auxiliaries

Developed by Ellman, these chiral sulfinamides have found widespread use in diastereoselective alkylations, the synthesis of protected chiral amines, the Strecker synthesis of α-alkyl α-amino acids, ...
Aldrich ChemFiles 2005, 5.4, 8.
Keywords: Addition reactions, Alkylations, Asymmetric synthesis, Catalysis, Chemfiles, Hydrogenations, Infrared spectroscopy, Ligands, Strecker synthesis

Related Content

Ellman's Sulfinamides in chemical Synthesis

Since its introduction by Ellman in 1997 as a chiral ammonia equivalent,1 enantiopure 2-methyl-2-propanesulfinamide (tert-butanesulfinamide) has been demonstrated to be a versatile chiral auxiliary a...
Keywords: Antibiotics, Asymmetric synthesis, Condensations, Cyclizations, Ligands, Reductions

Peer-Reviewed Papers
15

References

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