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Literature DB >> 17203133

A highly enantio- and diastereoselective 1,3-dimethylallylation of aldehydes.

Yu Yuan¹, Amy J Lai, Christina M Kraml, Chulbom Lee.

Abstract

A highly enantio- and diastereoselective pentenylation of aldehydes is described. The homoallylic alcohol derived from 1,3-dimethylallylation of (-)-menthone undergoes an efficient allyl-transfer reaction with a wide range of aliphatic aldehydes in the presence of an acid catalyst to give rise to the corresponding 4-methyl-2(E)-penten-4-yl-5-ol products in good yields with high enantio- and 4,5-syn-selectivities.

Entities: Chemical Gene

Year: 2006 PMID： 17203133 PMCID： PMC1761486 DOI： 10.1016/j.tet.2006.07.070

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

18 in total

1. The first and highly enantioselective crotylation of aldehydes via an allyl-transfer reaction from a chiral crotyl-donor.

Authors: J Nokami; M Ohga; H Nakamoto; T Matsubara; I Hussain; K Kataoka
Journal: J Am Chem Soc Date: 2001-09-19 Impact factor: 15.419

2. Strategic use of pinacol-terminated Prins cyclizations in target-oriented total synthesis.

Authors: Larry E Overman; Lewis D Pennington
Journal: J Org Chem Date: 2003-09-19 Impact factor: 4.354

3. Highly enantioselective Alk-2-enylation of aldehydes through an allyl-transfer reaction.

Authors: Junzo Nokami; Kenta Nomiyama; Seiji Matsuda; Nobuyuki Imai; Kazuhide Kataoka
Journal: Angew Chem Int Ed Engl Date: 2003-03-17 Impact factor: 15.336

4. A novel enantioselective (2Z)-alk-2-enylation of aldehydes via an allyl-transfer reaction from chiral allyl donors prepared from (+)-isomenthone.

Authors: Junzo Nokami; Kenta Nomiyama; Siddiqi M Shafi; Kazuhide Kataoka
Journal: Org Lett Date: 2004-04-15 Impact factor: 6.005

A highly enantio- and diastereoselective 1,3-dimethylallylation of aldehydes.

1. The first and highly enantioselective crotylation of aldehydes via an allyl-transfer reaction from a chiral crotyl-donor.

2. Strategic use of pinacol-terminated Prins cyclizations in target-oriented total synthesis.

3. Highly enantioselective Alk-2-enylation of aldehydes through an allyl-transfer reaction.

4. A novel enantioselective (2Z)-alk-2-enylation of aldehydes via an allyl-transfer reaction from chiral allyl donors prepared from (+)-isomenthone.

Review 5. Polyketide stereotetrads in natural products.

6. Utilization of an oxonia-Cope rearrangement as a mechanistic probe for Prins cyclizations.

7. Tetrahydropyran rings from a Mukaiyama-Michael cascade reaction.

8. New chiral synthons for efficient introduction of bispropionates via stereospecific oxonia-cope rearrangements.

9. Oxonia-cope prins cyclizations: a facile method for the synthesis of tetrahydropyranones bearing quaternary centers.

10. Axial-selective prins cyclizations by solvolysis of alpha-bromo ethers.

1. Stereoselective synthesis of tertiary ethers through geometric control of highly substituted oxocarbenium ions.