Enantioenriched Bifunctional Crotylsilanes for the Asymmetric Synthesis of Orthogonally Protected 2‑Methyl-1,3-diols

Enantiomerically pure α-substituted crotylsilane reagents I and ent-I undergo asymmetric aldehyde crotylation followed by Ir(I)-catalyzed diastereoselective allylic etherification to give a variety of orthogonally protected 2-methyl-1,3-diols at the synthetically useful level of yields and stereosel...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2013-10, Vol.15 (19), p.5142-5145
Main Authors: Kim, Dongeun, Lee, Jae Seung, Lozano, Lucia, Kong, Suk Bin, Han, Hyunsoo
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Enantiomerically pure α-substituted crotylsilane reagents I and ent-I undergo asymmetric aldehyde crotylation followed by Ir(I)-catalyzed diastereoselective allylic etherification to give a variety of orthogonally protected 2-methyl-1,3-diols at the synthetically useful level of yields and stereoselectivity. The reagents are air-stable and bifunctional so that they can be used in these reactions sequentially without recourse to functional group adjustments.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4026167