Diastereoselective manipulations of bicyclo[m.1.0]alkane derivatives. 5. α'-Alkylations of bicycle[m.1.0]alkan-2-ones

Eugene A Mash, James A. Baron, Timothy M. Gregg, Sandeep K. Nimkar

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

α'-Alkylations of bicyclo[m.1.0]alkan-2-ones were shown to proceed with high diastereoselectivity under conditions which favor kinetic control of the product distribution. Product yields for active electrophiles were good to very good. In sequential α'-alkylations with different electrophiles, reversal of the order of alkylation switches the configuration of the newly formed quaternary center.

Original languageEnglish (US)
Pages (from-to)2669-2682
Number of pages14
JournalTetrahedron
Volume54
Issue number12
DOIs
StatePublished - Mar 19 1998

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Alkanes
Bicycles
Alkylation
Derivatives
Switches
Kinetics

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Diastereoselective manipulations of bicyclo[m.1.0]alkane derivatives. 5. α'-Alkylations of bicycle[m.1.0]alkan-2-ones. / Mash, Eugene A; Baron, James A.; Gregg, Timothy M.; Nimkar, Sandeep K.

In: Tetrahedron, Vol. 54, No. 12, 19.03.1998, p. 2669-2682.

Research output: Contribution to journalArticle

Mash, Eugene A ; Baron, James A. ; Gregg, Timothy M. ; Nimkar, Sandeep K. / Diastereoselective manipulations of bicyclo[m.1.0]alkane derivatives. 5. α'-Alkylations of bicycle[m.1.0]alkan-2-ones. In: Tetrahedron. 1998 ; Vol. 54, No. 12. pp. 2669-2682.
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