Control of Chemo-, Regio-, and Enantioselectivity in Copper Hydride Reductions of Morita-Baylis-Hillman Adducts.

Title Control of Chemo-, Regio-, and Enantioselectivity in Copper Hydride Reductions of Morita-Baylis-Hillman Adducts.
Authors R.T.H. Linstadt; C.A. Peterson; C.I. Jette; Z.V. Boskovic; B.H. Lipshutz
Journal Org Lett
DOI 10.1021/acs.orglett.6b03464
Abstract

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 ?-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.

Citation R.T.H. Linstadt; C.A. Peterson; C.I. Jette; Z.V. Boskovic; B.H. Lipshutz.Control of Chemo-, Regio-, and Enantioselectivity in Copper Hydride Reductions of Morita-Baylis-Hillman Adducts.. Org Lett. 2017;19(2):328331. doi:10.1021/acs.orglett.6b03464

Related Elements

Copper

See more Copper products. Copper Bohr Model Copper (atomic symbol: Cu, atomic number: 29) is a Block D, Group 11, Period 4 element with an atomic weight of 63.546. The number of electrons in each of copper's shells is 2, 8, 18, 1 and its electron configuration is [Ar]3d10 4s1. The copper atom has a radius of 128 pm and a Van der Waals radius of 186 pm. Copper was first discovered by Early Man prior to 9000 BC. In its elemental form, copper has a reddish-orange metallic and lustrous appearance. Of all pure metals, only silver Elemental Copperhas a higher electrical conductivity. The origin of the word copper comes from the Latin word 'cuprium' which translates as "metal of Cyprus," as the Mediterranean island of Cyprus was known as an ancient source of mined copper..

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