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Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis : Novel ...

Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis : Novel ...

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Ref.459<br />

Ar<br />

Ar<br />

HF 2 −<br />

HF 2 −<br />

+<br />

N<br />

+<br />

N<br />

A′<br />

SILYLATION OF NITRO COMPOUNDS AS A PROCESS 617<br />

A<br />

Ref.460<br />

Ar<br />

CF 3<br />

F 3C<br />

CF 3<br />

Ar −<br />

Ref.462<br />

CF 3<br />

Ar −<br />

CF 3<br />

or<br />

CF 3<br />

CF 3<br />

R 2<br />

syn/anti ~ 82/18<br />

syn (ee 97%)<br />

anti (ee 78%)<br />

CHO<br />

F3C +<br />

O<br />

R 1<br />

R 1<br />

A′<br />

OSiMe 3<br />

N<br />

R 3<br />

NO 2<br />

R 3<br />

R 2<br />

OSiMe 3<br />

yield 75%–90%<br />

anti/syn ≥ 92:1<br />

97% > ee > 88%<br />

O<br />

+<br />

R 1<br />

R<br />

O OSiMe3 1<br />

N<br />

OSiMe 3<br />

NO 2<br />

NO 2<br />

R1 = Me; R2 = Ph.<br />

yield 92%, ee 95%<br />

R 2 O<br />

O<br />

R 2<br />

R 1<br />

R 1<br />

+<br />

N<br />

OH<br />

H<br />

OSiMe3<br />

Scheme 3.196

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