Highly Diastereoselective Oxy-Michael Additions of Enantiopureδ-Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2-Amino Alcohols

Nicola J. Adderley; David J. Buchanan; Darren J. Dixon; Dramane I. Lainé

doi:10.1002/anie.200352007

Highly Diastereoselective Oxy-Michael Additions of Enantiopureδ-Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2-Amino Alcohols

Angewandte Chemie International Edition ◽

10.1002/anie.200352007 ◽

2003 ◽

Vol 42 (35) ◽

pp. 4241-4244 ◽

Cited By ~ 42

Author(s):

Nicola J. Adderley ◽

David J. Buchanan ◽

Darren J. Dixon ◽

Dramane I. Lainé

Keyword(s):

Asymmetric Synthesis ◽

Amino Alcohols ◽

Michael Additions

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Highly Diastereoselective Oxy-Michael Additions of Enantiopureδ-Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2-Amino Alcohols

Angewandte Chemie ◽

10.1002/ange.200352007 ◽

2003 ◽

Vol 115 (35) ◽

pp. 4373-4376 ◽

Cited By ~ 9

Author(s):

Nicola J. Adderley ◽

David J. Buchanan ◽

Darren J. Dixon ◽

Dramane I. Lainé

Keyword(s):

Asymmetric Synthesis ◽

Amino Alcohols ◽

Michael Additions

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Highly Diastereoselective Oxy-Michael Additions of Enantiopure δ-Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2-Amino Alcohols.

ChemInform ◽

10.1002/chin.200352082 ◽

2003 ◽

Vol 34 (52) ◽

Author(s):

Nicola J. Adderley ◽

David J. Buchanan ◽

Darren J. Dixon ◽

Dramane I. Laine

Keyword(s):

Asymmetric Synthesis ◽

Amino Alcohols ◽

Michael Additions

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Chiral amino alcohols derived from (S)-6-chloronicotine as catalysts for asymmetric synthesis

Tetrahedron Letters ◽

10.1016/j.tetlet.2009.02.012 ◽

2009 ◽

Vol 50 (16) ◽

pp. 1806-1808 ◽

Cited By ~ 14

Author(s):

Sonja S. Capracotta ◽

Daniel L. Comins

Keyword(s):

Asymmetric Synthesis ◽

Amino Alcohols ◽

Chiral Amino Alcohols

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ChemInform Abstract: The Asymmetric Synthesis of β-Lactams. Stereocontrolled Asymmetric Tandem Michael Additions and Alkylations of α,β-Unsaturated Acyl Ligands Bound to the Chiral Auxiliary [η5-C5H5)Fe(CO)(PPh3)].

Chemischer Informationsdienst ◽

10.1002/chin.198650212 ◽

1986 ◽

Vol 17 (50) ◽

Author(s):

S. G. DAVIES ◽

I. M. DORDOR-HEDGECOCK ◽

K. H. SUTTON ◽

J. C. WALKER

Keyword(s):

Asymmetric Synthesis ◽

Chiral Auxiliary ◽

Michael Additions ◽

Unsaturated Acyl

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ChemInform Abstract: Asymmetric Synthesis of Fluorine-Containing Amines, Amino Alcohols, α- and β-Amino Acids Mediated by Chiral Sulfinyl Group

ChemInform ◽

10.1002/chin.201021225 ◽

2010 ◽

Vol 41 (21) ◽

pp. no-no

Author(s):

Alexander E. Sorochinsky ◽

Vadim A. Soloshonok

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Amino Alcohols ◽

Sulfinyl Group

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Chiral β-Amino Alcohols and Derivatives in the Asymmetric Synthesis of Tetrahydroisoquinolines

ChemInform ◽

10.1002/chin.200431261 ◽

2004 ◽

Vol 35 (31) ◽

Author(s):

Eneritz Anakabe ◽

Dolores Badia ◽

Luisa Carrillo ◽

Efraim Reyes ◽

Jose L. Vicario

Keyword(s):

Asymmetric Synthesis ◽

Amino Alcohols

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Development and Application of a New General Method for the Asymmetric Synthesis ofsyn- andanti-1,3-Amino Alcohols

Journal of the American Chemical Society ◽

10.1021/ja0363462 ◽

2003 ◽

Vol 125 (37) ◽

pp. 11276-11282 ◽

Cited By ~ 119

Author(s):

Takuya Kochi ◽

Tony P. Tang ◽

Jonathan A. Ellman

Keyword(s):

Asymmetric Synthesis ◽

Amino Alcohols ◽

General Method

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ChemInform Abstract: Asymmetric Synthesis of Pyridylethanols and Amino Alcohols by Enantioselective Reduction with Lithium Borohydride Modified with N,N′-Dibenzoylcystine.

ChemInform ◽

10.1002/chin.198748201 ◽

1987 ◽

Vol 18 (48) ◽

Author(s):

K. SOAI ◽

S. NIWA ◽

T. KOBAYASHI

Keyword(s):

Asymmetric Synthesis ◽

Amino Alcohols ◽

Lithium Borohydride ◽

Enantioselective Reduction

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Regioselective and Diastereoselective Allylic Amination Using Chlorosulfonyl Isocyanate. A Novel Asymmetric Synthesis of Unsaturated Aromatic 1,2-Amino Alcohols.

ChemInform ◽

10.1002/chin.200336021 ◽

2003 ◽

Vol 34 (36) ◽

Author(s):

Ji Duck Kim ◽

Ok Pyo Zee ◽

Young Hoon Jung

Keyword(s):

Asymmetric Synthesis ◽

Amino Alcohols ◽

Allylic Amination ◽

Chlorosulfonyl Isocyanate

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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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