A Magnesium-Based Diastereoselective Preparation of Pyridylic 1,3-Amino Alcohols Using the tert-Butyl Sulfinamide Auxiliary

Fjelbye, Kasper; Svenstrup, Niels; Püschl, Ask

doi:10.1055/s-0034-1378854

Cited by 8 publications

(1 citation statement)

References 26 publications

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“…Fjelbye et al prepared a chiral 1,3-amino alcohol (as hydrochloride salt) using a two-step approach involving the magnesiation of 2-iodopyridine in 2-MeTHF followed by the reaction with the chiral sulfinamide direct precursor of the desired enantiopure compound [62]. The following points merit mention: (a) the use of the Turbo Grignard reagent ( i -PrMgCl LiCl) guarantees the avoiding of homocoupled products; (b) 2-MeTHF is the optimal solvent in terms of both reaction yield and, more importantly, diastereoselectivity (Scheme 6).…”

Section: Use Of 2-methf In Reactions Involving Carbanionic and Nucleomentioning

confidence: 99%

Recent advancements on the use of 2-methyltetrahydrofuran in organometallic chemistry

et al. 2016

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Since the introduction of 2-methyltetrahydrofuran as an useful alternative to the classical tetrahydrofuran, there has been a continuous interest in the synthetic community operating at academic and industrial towards it. In particular, the much higher stability that basic organometallic reagents display in 2-methyltetrahydrofuran makes it suitable for processes involving such sensitive species including asymmetric transformations. The easy formation of an azeotropic mixture with water, the substantial immiscibility with water, and the fact it derives from natural sources (corncobs or bagasse), allow to consider it in agreement with the Anastas’ Geen Chemistry principles. In this minireview, selected examples of its employment in organometallic transformations ranging from carbanions to radical and transition metal-catalyzed processes are provided.Graphical abstract

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Section: Use Of 2-methf In Reactions Involving Carbanionic and Nucleomentioning

confidence: 99%

Recent advancements on the use of 2-methyltetrahydrofuran in organometallic chemistry

et al. 2016

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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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ChemInform Abstract: A Magnesium‐Based Diastereoselective Preparation of Pyridylic 1,3‐Amino Alcohols Using the tert‐Butyl Sulfinamide Auxiliary.

2016

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A Magnesium-Based Diastereoselective Preparation of Pyridylic 1,3-Amino Alcohols Using the tert-Butyl Sulfinamide Auxiliary

Abstract: 1,3-Amino alcohols were prepared by using a two-step approach and an interesting reversal in diastereoselectivity is discussed.

Cited by 8 publications

References 26 publications

Recent advancements on the use of 2-methyltetrahydrofuran in organometallic chemistry

Recent advancements on the use of 2-methyltetrahydrofuran in organometallic chemistry

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

ChemInform Abstract: A Magnesium‐Based Diastereoselective Preparation of Pyridylic 1,3‐Amino Alcohols Using the tert‐Butyl Sulfinamide Auxiliary.

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