Literature DB >> 12967278

Unexpected syn hydride migration in the non-aldol aldol reaction.

Michael E Jung1, Alexandra van den Heuvel, Andrew G Leach, K N Houk.   

Abstract

[structure: see text] Non-aldol aldol rearrangement of the epoxy silyl ether 13b afforded the expected anti methyl ketone 14, while the diastereomeric epoxy silyl ether 13a afforded the syn methyl ketone 8b via an unprecedented syn hydride migration. Calculations suggest that this unusual reaction proceeds via the carbocation, which cannot easily rotate due to steric hindrance.

Entities:  

Mesh：

Substances：

Year:  2003        PMID： 12967278     DOI： 10.1021/ol0350801

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  Computational elucidation of the origins of reactivity and selectivity in non-aldol aldol rearrangements of cyclic epoxides.

Authors:  Hao Wang; K N Houk; Damian A Allen; Michael E Jung
Journal:  Org Lett       Date:  2011-05-13       Impact factor: 6.005

2.  Asymmetric synthesis of anti-aldol segments via a nonaldol route: synthetic applications to statines and (-)-tetrahydrolipstatin.

Authors:  Arun K Ghosh; Khriesto Shurrush; Sarang Kulkarni
Journal:  J Org Chem       Date:  2009-06-19       Impact factor: 4.354

3.  Total syntheses of (+)- and (-)-peribysin E.

Authors:  Angie R Angeles; Stephen P Waters; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2008-09-11       Impact factor: 15.419
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.