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497401

Sigma-Aldrich

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

98%

Synonym(s):

(R)-2-methyl-2-propanesulfinamide, (R)-2-methylpropane-2-sulfinamide, (R)-tert-butanesulfinamide, (R)-tert-butylsulfinamide

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About This Item

Linear Formula:
(CH3)3CS(O)NH2
CAS Number:
196929-78-9
Molecular Weight:
121.20
MDL number:
MFCD05861479
UNSPSC Code:
12352111
PubChem Substance ID:
24873117
NACRES:
NA.22

Quality Level

100

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

SMILES string

CC(C)(C)S(N)=O

InChI

1S/C4H11NOS/c1-4(2,3)7(5)6/h5H2,1-3H3/t7-/m1/s1

InChI key

CESUXLKAADQNTB-SSDOTTSWSA-N

Related Categories

General description

(R)-(+)-2-Methyl-2-propanesulfinamide is a chiral auxiliary used in the condensation of the aldehyde.

Application

Ellman′s Sulfinamides
(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.
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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Bram Denolf et al.
Organic letters, 8(14), 3129-3132 (2006-06-30)
[reaction: see text] Reaction of chiral alpha-chloro tert-butanesulfinyl aldimines with Grignard reagents efficiently afforded beta-chloro N-sulfinamides in high diastereomeric excess. The latter compounds were cyclized toward the corresponding chiral aziridines in a high-yielding one-pot reaction or after separate treatment with
Asymmetric synthesis of a, a-difluoro-?-amino acid derivatives from enantiomerically pure N-tert-butylsulfinimines.
Staas, DD, et al.
The Journal of Organic Chemistry, 67(23), 8276-8279 (2002)
Dong Pei et al.
Organic letters, 8(25), 5913-5915 (2006-12-01)
Easily accessible chiral sulfinamide 2 has been developed as the first highly efficient and enantioselective organocatalyst relying solely on a chiral sulfur center for stereochemical induction. In the presence of 20 mol % of 2, a broad range of N-aryl
Jeffrey P McMahon et al.
Organic letters, 6(10), 1645-1647 (2004-05-07)
Addition of alkyl or aryl Grignard reagents to N-sulfinyl imines derived from 3- and 4-substituted cyclohexanones proceeds with good yields and with excellent diasteroselectivity. The selectivity of the reaction is controlled by the ring substituent rather than the sulfinyl group
A stereoselective synthesis of (S)-2-(((3-fluoro-4-methylphenoxy) carbonyl)(1-(4-((5-methyl-2-phenyloxazol-4-yl) methoxy) phenyl) ethyl) amino) acetic acid, a highly potent PPAR alpha gamma dual agonist
Xinhua Q et al.
Tetrahedron, 71, 9408-9414 (2015)
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Articles

Ellman's Sulfinamides

Ellman's sulfinamide is available in both enantiomeric and racemic forms for your research. This versatile and useful auxiliary has found extensive use both in academics and industry.

Related Content

Ellman Group – Professor Product Portal

The Ellman group has participated in the development of a variety of C-H functionalization methods. An electron rich phosphine ligand has proven to be very useful for a variety of Rh(I)-catalyzed C-C bond forming reactions applicable to heterocycle synthesis as exemplified in the recent Science paper “Proton Donor Acidity Controls Selectivity in Nonaromatic Nitrogen Heterocycle Synthesis.” Another useful ligand developed for the highly functional group compatible direct arylation of nitrogen heterocycles is described in a 2008 J. Am. Chem. Soc. paper “Rh(I)-Catalyzed Arylation of Heterocycles via C-H Bond Activation: Expanded Scope through Mechanistic Insight.” The Ellman group also developed the chiral amine reagent tert-Butanesulfinamide, which is extensively used in academics and industry for the asymmetric synthesis of amines. A comprehensive survey of tert-Butanesulfinamide methods and applications up through 2009 is provided in the 2010 Chemical Reviews article, “Synthesis and Applications of tert-Butanesulfinamide.”

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