Stereoselective Synthesis of Highly Substituted Cyclohexanes by a Rhodium-Carbene Initiated Domino Sequence

A stereoselective synthesis of cyclohexanes bearing four stereocenters from vinyldiazoacetates and allyl alcohols by a rhodium-carbene initiated domino reaction is described. The reaction cascade features a tandem ylide formation/[2,3]-sigmatropic rearrangement, oxy-Cope rearrangement, and type II c...

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Veröffentlicht in:	Organic letters 2015-02, Vol.17 (4), p.794-797
Hauptverfasser:	Parr, Brendan T, Davies, Huw M. L
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Cyclohexanes - chemical synthesis Cyclohexanes - chemistry Molecular Structure Propanols - chemistry Rhodium - chemistry Stereoisomerism
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description	A stereoselective synthesis of cyclohexanes bearing four stereocenters from vinyldiazoacetates and allyl alcohols by a rhodium-carbene initiated domino reaction is described. The reaction cascade features a tandem ylide formation/[2,3]-sigmatropic rearrangement, oxy-Cope rearrangement, and type II carbonyl ene reaction, all of which proceed with a high degree of stereocontrol. The products are routinely isolated with excellent stereocontrol (>97:3 dr, 99% ee).
doi_str_mv	10.1021/ol503508k
format	Article
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L</creatorcontrib><title>Stereoselective Synthesis of Highly Substituted Cyclohexanes by a Rhodium-Carbene Initiated Domino Sequence</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A stereoselective synthesis of cyclohexanes bearing four stereocenters from vinyldiazoacetates and allyl alcohols by a rhodium-carbene initiated domino reaction is described. The reaction cascade features a tandem ylide formation/[2,3]-sigmatropic rearrangement, oxy-Cope rearrangement, and type II carbonyl ene reaction, all of which proceed with a high degree of stereocontrol. 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subjects	Catalysis Cyclohexanes - chemical synthesis Cyclohexanes - chemistry Molecular Structure Propanols - chemistry Rhodium - chemistry Stereoisomerism
title	Stereoselective Synthesis of Highly Substituted Cyclohexanes by a Rhodium-Carbene Initiated Domino Sequence
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