A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide

Barrow, James C.; Ngo, Phung L.; Pellicore, Janetta M.; Selnick, Harold G.; Nantermet, Philippe G.

doi:10.1016/s0040-4039(01)00122-8

Cited by 78 publications

(53 citation statements)

References 17 publications

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“…The utility of tert-butanesulfinamide for the asymmetric synthesis of amines is clearly indicated by its extensive use by other researchers. For example, reports have appeared from Olah and Prakash on the highly efficient synthesis of α-trifluoromethylamines [17], Davis on the asymmetric synthesis of α-amino acids [18], Mabic on the asymmetric synthesis of 1,2-diamines [19], Barrow on the asymmetric synthesis of 1,2-amino alcohols [13], Silverman on novel applications to support-bound β-amino acids [20], and researchers at Astra Zeneca, Separacor, and Merck on the asymmetric synthesis of α-branched amines [21], α,α-dibranched amines [22], and β-amino acids [23] for drug discovery applications.…”

Section: Resultsmentioning

confidence: 99%

“…For this reason, both my group [12] and Barrow and coworkers at Merck [13] have explored the asymmetric synthesis of this compound class by the 1,2-addition of organometallic reagents to α-alkoxy sulfinyl imines. The addition of Grignard reagents to α-silyloxy tert-butanesulfinyl aldimines proceeds in high yields (85-96 %) and selectivities (83:17-96:4) in the noncoordinating solvents toluene and CH 2 Cl 2 (eq.…”

Section: Asymmetric Synthesis Of 12-amino Alcoholsmentioning

confidence: 99%

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Applications of tert‐Butanesulfinamide in the Asymmetric Synthesis of Amines

Ellman

2003

ChemInform

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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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Section: Resultsmentioning

confidence: 99%

Section: Asymmetric Synthesis Of 12-amino Alcoholsmentioning

confidence: 99%

Applications of tert‐Butanesulfinamide in the Asymmetric Synthesis of Amines

Ellman

2003

ChemInform

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“…[42] Later, Wang's group developed an improved version of this reaction by changing the hydroxyl protecting group of sulfinimine 55 to the tert-butyldiphenylsilyl (TBDS) group and using alkynylmagnesium chloride instead of the bromide. [43] These modifications resulted in almost exclusive formation of anti-Ellman diastereomer 56b (dr >1:99) in the addition reactions of Grignard reagents derived from phenyl-, TMS-, and n-propylacetylene to sulfinimine 55.…”

Section: Addition To N-sulfinyliminesmentioning

confidence: 99%

Synthesis of α‐Ethynyl Glycines

Boļšakova

Jirgensons

2016

Eur J Org Chem

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α-Ethynyl glycine derivatives have a high potential for functionalization by derivatization of the amino acid or acetylene moiety, and, as a result, are important intermediates in the construction of biologically active compounds, including natural products. The main methods for the synthesis of ethynyl glycines and glycinols can be divided into six different transformations: (a) homologations of serinal derivatives, (b) nucleophilic alkynylations of α-imino esters/alcohols or their precur-

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“…However, this model correctly explained the facial selectivity of addition with allyl zinc to an aryl sulfinylimine (in THF). 43 In contrast, the Barrow chelation model TS-6, 46 involving chelation…”

Section: S-10smentioning

confidence: 99%

Stereoselectivity of the Honda–Reformatsky Reaction in Reactions with Ethyl Bromodifluoroacetate with α-Oxygenated Sulfinylimines

et al. 2014

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Abstract-The Reformatsky reaction of ethyl bromodifluoroacetate to α-oxygenated sulfinylimines is described. Using Honda-Reformatsky conditions, the reaction proceeds with double diastereodifferentiation, with the configuration of the sulfinyl group determining the stereochemical course of the reaction. Excellent diastereoselectivities (>94:6) are obtained for the matched cases. In contrast, reaction with sulfinylimines derived from unsubstituted alkanals proceeded with virtually no diastereoselectivity.

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A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide

Cited by 78 publications

References 17 publications

Applications of tert‐Butanesulfinamide in the Asymmetric Synthesis of Amines

Applications of tert‐Butanesulfinamide in the Asymmetric Synthesis of Amines

Synthesis of α‐Ethynyl Glycines

Stereoselectivity of the Honda–Reformatsky Reaction in Reactions with Ethyl Bromodifluoroacetate with α-Oxygenated Sulfinylimines

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