Highly diastereoselective addition of silyldihalomethyllithiums to chiral alkyl esters.

Abstract:

:Treatment of benzoate, formate, or trifluoroacetate esters with silyldibromomethyllithiums provides alkyl silyl mixed acetals via the 1,3-rearrangement of a silyl group from carbon to oxygen. A high level of asymmetric induction onto the acetal carbon is observed when chiral alkyl esters are employed. The stereochemical assignment of the silyl acetal 13j was accomplished on the basis of X-ray crystallographic analysis. A one-pot synthesis of a three-component coupling product R(1)C(OR(2))(OSiMe(2)-t-Bu)CX(2)E' (X = Cl, Br) by sequential additions of an ester (R(1)CO(2)R(2)) and the second electrophile was achieved.

journal_name

Chirality

journal_title

Chirality

authors

Shinokubo H,Kondo J,Inoue A,Oshima K

doi

10.1002/chir.10152

subject

Has Abstract

pub_date

2003-01-01 00:00:00

pages

31-7

issue

1

eissn

0899-0042

issn

1520-636X

journal_volume

15

pub_type

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