Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition toN-tert-Butanesulfinyl α-Alkoxyaldimines

Jared W. Evans; Jonathan A. Ellman

doi:10.1021/jo035224p

Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition toN-tert-Butanesulfinyl α-Alkoxyaldimines

The Journal of Organic Chemistry ◽

10.1021/jo035224p ◽

2003 ◽

Vol 68 (26) ◽

pp. 9948-9957 ◽

Cited By ~ 53

Author(s):

Jared W. Evans ◽

Jonathan A. Ellman

Keyword(s):

Nucleophilic Addition ◽

Stereoselective Synthesis ◽

Amino Alcohols

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Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to N-tert-Butanesulfinyl α-Alkoxyaldimines.

ChemInform ◽

10.1002/chin.200419070 ◽

2004 ◽

Vol 35 (19) ◽

Author(s):

Jared W. Evans ◽

Jonathan A. Ellman

Keyword(s):

Nucleophilic Addition ◽

Stereoselective Synthesis ◽

Amino Alcohols

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Direct Stereoselective Synthesis of Enantiomerically Pure anti-β-Amino Alcohols

The Journal of Organic Chemistry ◽

10.1021/jo500481j ◽

2014 ◽

Vol 79 (15) ◽

pp. 6775-6782 ◽

Cited By ~ 22

Author(s):

Gastón Silveira-Dorta ◽

Osvaldo J. Donadel ◽

Víctor S. Martín ◽

José M. Padrón

Keyword(s):

Stereoselective Synthesis ◽

Amino Alcohols ◽

Enantiomerically Pure

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ChemInform Abstract: Stereoselective Synthesis of 1,3-Amino Alcohols by the Pd-Catalyzed Cyclization of Trichloroacetimidates.

ChemInform ◽

10.1002/chin.201429197 ◽

2014 ◽

Vol 45 (29) ◽

pp. no-no

Author(s):

Yuanzhen Xie ◽

Kai Yu ◽

Zhenhua Gu

Keyword(s):

Stereoselective Synthesis ◽

Amino Alcohols

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Stereoselective synthesis of anti-2-oxazolidinones by Ph3P–CCl4–Et3N mediated SN2 cyclization of N-Boc-β-amino alcohols

Tetrahedron Letters ◽

10.1016/s0040-4039(03)01508-9 ◽

2003 ◽

Vol 44 (33) ◽

pp. 6323-6325 ◽

Cited By ~ 9

Author(s):

G Madhusudhan ◽

G Om Reddy ◽

J Ramanatham ◽

P.K Dubey

Keyword(s):

Stereoselective Synthesis ◽

Amino Alcohols

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Stereoselective Synthesis of Enantipure β-Amino Alcohols via Nucleophilic β-Amino-α-hydroxyalkylation by Means of 1-Lithiated 2-[N-(Diphenylmethyleneamino)]alkyl Carbamates

Synthesis ◽

10.1055/s-1997-1155 ◽

1997 ◽

Vol 1997 (02) ◽

pp. 176-182 ◽

Cited By ~ 6

Author(s):

Christiane Boie ◽

Dieter Hoppe

Keyword(s):

Stereoselective Synthesis ◽

Amino Alcohols

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ChemInform Abstract: Stereoselective Synthesis of Trifluoromethylated Compounds: Nucleophilic Addition of Formaldehyde N,N-Dialkylhydrazones to Trifluoromethyl Ketones.

ChemInform ◽

10.1002/chin.200013081 ◽

2010 ◽

Vol 31 (13) ◽

pp. no-no

Author(s):

Carmen Pareja ◽

Eloisa Martin-Zamora ◽

Rosario Fernandez ◽

Jose M. Lassaletta

Keyword(s):

Nucleophilic Addition ◽

Stereoselective Synthesis ◽

Trifluoromethyl Ketones

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Applications of tert-butanesulfinamide in the asymmetric synthesis of amines

Pure and Applied Chemistry ◽

10.1351/pac200375010039 ◽

2003 ◽

Vol 75 (1) ◽

pp. 39-46 ◽

Cited By ~ 181

Author(s):

J. A. Ellman

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Nucleophilic Addition ◽

Amino Alcohols ◽

Wide Range ◽

Aldehydes And Ketones ◽

Directing Group ◽

High Yields ◽

Direct Condensation

tert-Butanesulfinamide is prepared using catalytic enantioselective methods in two steps from the extremely inexpensive oil waste by-product, tert-butyl disulfide. Direct condensation of tert-butanesulfinamide with aldehydes and ketones provides tert-butanesulfinyl imines in uniformly high yields. The tert-butanesulfinyl group activates the imines for the addition of many different classes of nucleophiles, serves as a powerful chiral directing group, and after nucleophilic addition is readily cleaved by treatment with acid. A wide range of highly enantioenriched amines, including α-branched and α,α-dibranched amines, α- and β-amino acids, 1,2 and 1,3-amino alcohols and α-trifluoromethyl amines are efficiently synthesized using this methodology.

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