Control of Chemo‑, Regio‑, and Enantioselectivity in Copper Hydride Reductions of Morita–Baylis–Hillman Adducts

Nonracemically ligated copper hydride can be used to effect tandem SN2′/1,2-reductions of racemic Morita–Baylis–Hillman (MBH) acetates to access enantioenriched chiral allylic alcohols with defined olefin geometry. MBH esters, including those with β-substitution, can be transformed to stereodefined...

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Bibliographic Details
Published inOrganic letters Vol. 19; no. 2; pp. 328 - 331
Main Authors Linstadt, Roscoe T. H, Peterson, Carl. A, Jette, Carina I, Boskovic, Zarko V, Lipshutz, Bruce H
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.01.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
AGENT
ACTIVATION
ASYMMETRIC HYDROSILYLATIONS
CONJUGATE REDUCTION
SI-B BOND
ALLYLIC SUBSTITUTION
SILYLATION
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Summary:Nonracemically ligated copper hydride can be used to effect tandem SN2′/1,2-reductions of racemic Morita–Baylis–Hillman (MBH) acetates to access enantioenriched chiral allylic alcohols with defined olefin geometry. MBH esters, including those with β-substitution, can be transformed to stereodefined enoates by taking advantage of a bulky, oligomeric, in situ generated trialkoxysiloxane leaving group. Finally, an atypical conversion of easily arrived at MBH alcohol derivatives to nonracemic allylic alcohols is disclosed.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b03464