Stereoselective Addition of 2-Phenyloxazol-4-yl Trifluoromethanesulfonate to <i>N</i>-Sulfinyl Imines: Application to the Synthesis of the HCV Protease Inhibitor Boceprevir

Morris, William; Muppalla, Kiran; Cowden, Cameron J.; Ball, Richard G.

doi:10.1021/jo301856f

Cited by 6 publications

(6 citation statements)

References 44 publications

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“…They were stored at room temperature for several months. Unfortunately, when we ran 13 C NMR experiments, we found the HCl salts of (R)-2a, (S)-2f, and (R)-2f were not stable under such storage conditions. Near full demethylation of (R)-2a happened during storage (see the Supporting Information for NMR spectra).…”

Section: Scheme 5 Dehalogenation Of Chloro Derivative 2dmentioning

confidence: 93%

“…1 H NMR spectra were recorded at 300 or 400 MHz as indicated. 13 C NMR spectra were recorded at 75 or 101 MHz as indicated. Diastereomeric ratio (dr) values were determined by mass balance of isolated diastereomers.…”

Section: Paper Syn Thesismentioning

confidence: 99%

“…Because all 1,2-addition intermediates were consumed, some of the addition products are reported with LCMS results, if available. Unfortunately, 13 C NMR was not recorded on them. In this paper, synthetic details of one diastereomer of the 1,2-addition intermediates from each entry are provided, while only a general procedure of deprotection for the synthesis of final amino alcohols is given.…”

Section: Paper Syn Thesismentioning

confidence: 99%

“…1 H NMR was recorded at WuXi AppTech, and 13 C NMR and other 2D NMR were recorded at Mölndal (AstraZeneca). 13 C NMR was reported based on 2D NMR study (please see the Supporting Information). 1…”

Section: (S)-2-amino-2-(6-methoxypyridin-3-yl)ethanol Dihydrochloridementioning

confidence: 99%

“…8 However, other 2-heteroaromatic-substituted 1,2-amino alcohols have been less explored despite being important building blocks from a drug discovery perspective. [9][10][11][12][13] The synthetic approaches in Schemes 1 and 2 were not felt to be suitable for medicinal chemists as they either only deliver one enantiomer or would require a lengthy synthetic sequence.…”

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confidence: 99%

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Synthesis of Enantiomerically Pure 2-Heteroaromatic-Substituted 1,2-Amino Alcohols from Chiral tert-Butanesulfinyl Aldimines

et al. 2014

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Nine R/S pairs of 2-heteroaromatic-substituted 1,2-amino alcohols were synthesized through 1,2-nucleophilic addition between chiral N-(tert-butylsulfinyl)imines and heteroaromatic carbanions. In most cases, the R S-isomer of N-(tert-butylsulfinyl)imines afforded the R amino alcohol from deprotection of the major diastereomer, and S Simines afforded the S product. In general, this procedure allows for the preparation of a variety of enantiomeric pairs of 2-heteroaromatic-substituted 1,2-amino alcohols on a practical scale (>10 g) in two steps in good yields.

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Section: Scheme 5 Dehalogenation Of Chloro Derivative 2dmentioning

confidence: 93%

Section: Paper Syn Thesismentioning

confidence: 99%

Section: Paper Syn Thesismentioning

confidence: 99%

Section: (S)-2-amino-2-(6-methoxypyridin-3-yl)ethanol Dihydrochloridementioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis of Enantiomerically Pure 2-Heteroaromatic-Substituted 1,2-Amino Alcohols from Chiral tert-Butanesulfinyl Aldimines

et al. 2014

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Addition of Non‐Stabilized Carbon‐Based Nucleophilic Reagents to ChiralN‐Sulfinyl Imines

et al. 2019

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Natural products and pharmaceuticals that contain chiral branched amines are compounds of considerable interest. One strategy for preparing chiral branched amines involves the addition of a nucleophile to an imine bearing a readily cleavable chiral auxiliary. Sulfinamide‐based auxiliaries are well‐suited to this approach because (i) many sulfonamides are commercially available or can be prepared by efficient synthetic methods, (ii) N ‐sulfinyl aldimines and ketimines can be prepared in a straightforward manner, (iii) the chiral amine products are obtained with high diastereomeric ratios across a wide range of carbon‐based nucleophiles, and (iv) the N ‐sulfinyl group is cleaved under mild conditions. This chapter focuses on the addition of non‐stabilized, carbon‐based nucleophiles to N ‐sulfinyl aldimines and ketimines. Specifically, additions of alkyl, alkenyl, aryl, allylic, propargylic, alkynyl, and cyano nucleophiles are presented. Factors that can influence the stereoselectivity of the addition reaction are presented, along with the most prevalent reaction conditions employed for each class of nucleophile. Nucleophilic additions to N ‐sulfinyl aldimines and ketimines are key steps in the syntheses of a number of drug discovery targets and natural products, examples of which are highlighted in this review.

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Chiral N‐tert‐Butylsulfinyl Imines: New Discoveries

Foubelo

Yus

2020

The Chemical Record

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In this account the reactions of chiral N‐tert‐butylsulfinyl imines with organometallic reagents such as organoalkaline (lithium, sodium, potassium and cesium derivatives), organomagnesium, organozinc, organoboron, organoaluminium, organoindium and organosilicon compounds is comprehensively described. The reactivity in all cases is derived to synthetic applications in order to prepare interesting organic nitrogenated molecules, especially in the field of alkaloid compounds.

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Stereoselective Addition of 2-Phenyloxazol-4-yl Trifluoromethanesulfonate to N-Sulfinyl Imines: Application to the Synthesis of the HCV Protease Inhibitor Boceprevir

Cited by 6 publications

References 44 publications

Synthesis of Enantiomerically Pure 2-Heteroaromatic-Substituted 1,2-Amino Alcohols from Chiral tert-Butanesulfinyl Aldimines

Synthesis of Enantiomerically Pure 2-Heteroaromatic-Substituted 1,2-Amino Alcohols from Chiral tert-Butanesulfinyl Aldimines

Addition of Non‐Stabilized Carbon‐Based Nucleophilic Reagents to ChiralN‐Sulfinyl Imines

Chiral N‐tert‐Butylsulfinyl Imines: New Discoveries

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