2022
DOI: 10.1016/j.tetlet.2022.153753
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Synthesis of optically pure, deuterated Maruoka Catalysts and their chemical reactivity

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Cited by 8 publications
(15 citation statements)
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“…In 2022, Maruoka and co-workers observed that the simplified Maruoka catalyst 200 , useful as a phase transfer catalyst for the asymmetric alkylation of amino acid derivatives, will undergo a base-promoted degradation via a [1,2]-Stevens rearrangement of ammonium ylide 201 (Scheme 26c ). 100 101 Interestingly, they showed that deuterium incorporation at the benzylic positions serves to impede the [1,2]-Stevens rearrangement, as demonstrated by a decreasing stability trend where, 200 < D 2 - 200 < D 4 - 200 , under the basic conditions of asymmetric alkylation reactions (Scheme 26d ). While this stability difference has clear implications for the utility of a more robust phase transfer catalysts, we highlight this [1,2]-Stevens rearrangement instance as deuterium incorporation may be useful in directing regioselective ammonium ylide formation in more complex settings.…”
Section: Selected Methodologymentioning
confidence: 99%
“…In 2022, Maruoka and co-workers observed that the simplified Maruoka catalyst 200 , useful as a phase transfer catalyst for the asymmetric alkylation of amino acid derivatives, will undergo a base-promoted degradation via a [1,2]-Stevens rearrangement of ammonium ylide 201 (Scheme 26c ). 100 101 Interestingly, they showed that deuterium incorporation at the benzylic positions serves to impede the [1,2]-Stevens rearrangement, as demonstrated by a decreasing stability trend where, 200 < D 2 - 200 < D 4 - 200 , under the basic conditions of asymmetric alkylation reactions (Scheme 26d ). While this stability difference has clear implications for the utility of a more robust phase transfer catalysts, we highlight this [1,2]-Stevens rearrangement instance as deuterium incorporation may be useful in directing regioselective ammonium ylide formation in more complex settings.…”
Section: Selected Methodologymentioning
confidence: 99%
“…In our previous communication, we studied the degradation process of catalyst 1 under basic, aqueous conditions (Figure 2). [9] Treatment of (S)-1 with an aqueous 50 % KOH/toluene mixture at room temperature (rt) for 2 h gave a tertiary amine 3 in 87 % yield through Stevens rearrangement. [9,22] Unlike catalyst 1, the treatment of (S,S)-2 did result in a Stevens rearrangement but gave a ring-expanded amine 4 in 64 % yield (Figure 3).…”
Section: Decomposition Of Chiral Phase-transfer Catalystsmentioning
confidence: 99%
“…To address this issue, we have recently communicated the synthesis and reactivity of the site-specifically deuteriumlabeled catalysts [D 4 ]1 and [D 2 ]1. [9] The design of these deuterated catalysts is based on our observation of the degradation process of catalyst 1 under basic conditions. 1 underwent the Stevens rearrangement through deprotonation at the benzylic positions.…”
Section: Introductionmentioning
confidence: 99%
“…Alkylamines, as related compounds, underwent direct deuteration at α ‐position, [6] α ‐ and β ‐positions, [7] and β ‐position [8] under adequate catalytic reaction conditions (Scheme 1‐A). The‐ α ‐position‐selective deuteration of tertiary ammonium salts using NaOD has also been reported [9] . However, we have continuously investigated multi‐deuteration (H/D exchange reaction) using heterogeneous catalysts (Pt/C, Ir/C, etc.)…”
Section: Introductionmentioning
confidence: 98%
“…The-α-position-selective deuteration of tertiary ammonium salts using NaOD has also been reported. [9] However, we have continuously investigated multideuteration (H/D exchange reaction) using heterogeneous catalysts (Pt/C, Ir/C, etc.) in mixed solvents of 2-PrOH and D 2 O as an inexpensive deuterium source.…”
Section: Introductionmentioning
confidence: 99%