Enantioselective synthesis of cyclopropane aminoalcohols containing quaternary stereogenic centers

Rifé, Joan; Ortuño, Rosa M.

doi:10.1016/s0957-4166(99)00463-2

Cited by 23 publications

(14 citation statements)

References 17 publications

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“…Another example of cyclization after ring-opening has been demonstrated by Riféand Ortunõ. 32 Aminocyclopropylaldehyde 16, generated under oxidative conditions, is unstable and readily undergoes ring-opening to form a zwitterionic intermediate. In this case, cyclization occurs upon the attack of the pendant enolate to give dihydrofuran derivative 17 (Scheme 6A).…”

Section: Acid and Base Promoted Reactivitymentioning

confidence: 99%

Selective Carbon–Carbon Bond Cleavage of Cyclopropylamine Derivatives

2020

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This review summarizes synthetic developments reported from 1987 to 2019 that exploit C–C single bond cleavage of cyclopropylamine-based systems. The synthetic and mechanistic aspects of key methodologies are highlighted, and examples where aminocyclopropanes are exploited as key intermediates in multistep synthesis are also discussed. The review encompasses cases where aminocyclopropanes participate in polar reactions, pericyclic processes, radical-based reactions, and C–C bond activations.

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Section: Acid and Base Promoted Reactivitymentioning

confidence: 99%

Selective Carbon–Carbon Bond Cleavage of Cyclopropylamine Derivatives

2020

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“…169,195,196 The MeCN (see Table 10, entries 3−4), a carbon-nitrogen bond is formed using pTSA in CH 2 Cl 2 (Scheme 80). Interestingly, the aminal products thus obtained can be converted into the C3- …”

Section: Scheme 70mentioning

confidence: 99%

Ring-opening, cycloaddition and rearrangement reactions of nitrogen-substituted cyclopropane derivatives

Rassadin

Six

2016

Tetrahedron

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“…Finally, cleavage of the N -Boc protective group in (1 R ,2 S )- 382 followed by treatment with propylene oxide provided the α-aminocyclopropanecarboxylic acid (1 R ,2 S )- 170 in excellent yield (Scheme 82). 181…”

Section: Synthesis Of 1-aminocycloalkanecarboxylic Acidsmentioning

confidence: 99%