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

doi:10.1016/S0040-4020(98)83003-2

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

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

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 language	English (US)
Pages (from-to)	2669-2682
Number of pages	14
Journal	Tetrahedron
Volume	54
Issue number	12
DOIs	https://doi.org/10.1016/S0040-4020(98)83003-2
State	Published - Mar 19 1998

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(98)83003-2

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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.",

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AU - Mash, Eugene A.

AU - Baron, James A.

AU - Gregg, Timothy M.

AU - Nimkar, Sandeep K.

PY - 1998/3/19

Y1 - 1998/3/19

N2 - 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.

AB - 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.

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

Abstract

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