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1 article(s) from Brayer, Jean-Louis

Sigmatropic rearrangements of cyclopropenylcarbinol derivatives. Access to diversely substituted alkylidenecyclopropanes

Guillaume Ernouf,
Jean-Louis Brayer,
Christophe Meyer and
Janine Cossy

Beilstein J. Org. Chem. 2019, 15, 333–350, doi:10.3762/bjoc.15.29

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Graphical Abstract

Scheme 1: Representative strategies for the formation of alkylidenecyclopropanes from cyclopropenes and scope...

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Scheme 2: [2,3]-Sigmatropic rearrangement of phosphinites 2a–h.

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Scheme 3: [2,3]-Sigmatropic rearrangement of a phosphinite derived from enantioenriched cyclopropenylcarbinol...

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Scheme 4: Selective reduction of phosphine oxide (E)-3f.

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Scheme 5: Attempted thermal [2,3]-sigmatropic rearrangement of phosphinite 6a.

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Scheme 6: Computed activation barriers and free enthalpies.

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Scheme 7: [2,3]-Sigmatropic rearrangement of phosphinites 6a–j.

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Scheme 8: Proposed mechanism for the Lewis base-catalyzed rearrangement of phosphinites 6.

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Scheme 9: [3,3]-Sigmatropic rearrangement of tertiary cyclopropenylcarbinyl acetates 10a–c.

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Scheme 10: [3,3]-Sigmatropic rearrangement of secondary cyclopropenylcarbinyl esters 10d–h.

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Scheme 11: [3,3]-Sigmatropic rearrangement of trichoroacetimidates 12a–i.

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Scheme 12: Reaction of trichloroacetamide 13f with pyrrolidine.

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Scheme 13: Catalytic hydrogenation of (arylmethylene)cyclopropropane 13f.

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Scheme 14: Instability of trichloroacetimidates 21a–c derived from cyclopropenylcarbinols 20a–c.

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Scheme 15: [3,3]-Sigmatropic rearrangement of cyanate 27 generated from cyclopropenylcarbinyl carbamate 26.

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Scheme 16: Synthesis of alkylidene(aminocyclopropane) derivatives 30–37 from carbamate 26.

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Scheme 17: Scope of the dehydration–[3,3]-sigmatropic rearrangement sequence of cyclopropenylcarbinyl carbamat...

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Scheme 18: Formation of trifluoroacetamide 50 from carbamate 49.

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Scheme 19: Formation of alkylidene[(N-trifluoroacetylamino)cyclopropanes] 51–54.

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Scheme 20: Diastereoselective hydrogenation of alkylidenecyclopropane 51.

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Scheme 21: Ireland–Claisen rearrangement of cyclopropenylcarbinyl glycolates 56a–l.

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Scheme 22: Synthesis and Ireland–Claisen rearrangement of glycolate 61 possessing gem-diester substitution at ...

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Scheme 23: Synthesis of alkylidene(gem-difluorocyclopropanes) 66a–h, and 66k–n from propargyl glycolates 64a–n....

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Scheme 24: Ireland–Claisen rearrangement of N,N-diBoc glycinates 67a and 67b.

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Scheme 25: Diastereoselective hydrogenation of alkylidenecyclopropanes 58a and 74.

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Scheme 26: Synthesis of functionalized gem-difluorocyclopropanes 76 and 77 from alkylidenecyclopropane 66a.

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Scheme 27: Access to oxa- and azabicyclic compounds 78–80.

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Review

Published 05 Feb 2019

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