A Convenient Route to Synthesize
N-Protected α,α-Difluorohomoallylic Amines
by gem-Difluoroallylation of α-Amido
Sulfones

Zheng-Feng Xie; Zhuo Chai; Gang Zhao; Ji-De Wang

doi:10.1055/s-0028-1083220

PAPER

A Convenient Route to Synthesize N-Protected α,α-Difluorohomoallylic Amines by gem-Difluoroallylation of α-Amido Sulfones

Zheng-Feng Xie^a, Zhuo Chai^b, Gang Zhao*^b, Ji-De Wang*^a
^a Education Ministry Key Laboratory of Oil & Gas Fine Chemicals, Xinjiang University, Urumqi 830046, P. R. of China
e-Mail: awangjdl@xju.edu.cn;
^b Key Laboratory of Organofluorine Chemistry and Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: zhaog@mail.sioc.ac.cn;

Abstract

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Abstract

A simple, mild, and efficient synthesis of α,α-difluorohomoallylic amines was achieved by the gem-difluoroallylation of α-amido sulfones with zinc powder.

Key words

fluorine compounds - allylations - amines - amido sulfones - zinc - ring-closing metathesis

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Referenzen

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8

Characterization data for 5: colorless crystals; mp 96-97 ˚C. IR (film): 2925, 2855, 1707, 1456, 1408, 1393, 1168, 1092, 698 cm^-¹. ^¹H NMR (300 MHz, CDCl₃): δ = 7.32 (m, 5 H), 6.26 (m, 1 H), 6.09 (m, 1 H), 5.74 (m, 1 H), 4.48-4.38 (m, 1 H), 3.56-3.47 (m, 13 H), 1.49 (s, 9 H). ^¹³C NMR (75 MHz, CDCl₃): δ = 154.1, 134.9, 133.6, 128.4, 128.2, 128.0, 122.1 (dd, J = 17.3, 25.1 Hz), 115.9 (t, J = 9 Hz), 120.6 (t, J = 177.5 Hz), 81.2, 59.1, 40.6, 27.2 (3 C). ^¹9F NMR (282 MHz, CDCl₃): δ = -79.56 (d, J _F,F = 279.2 Hz), -103.24 (d, J _F,F = 297.2 Hz). MS (ESI): m/z = 318 [M + Na]⁺. HRMS (EI): m/z calcd for C₁₁H₁₀NF₂ [M⁺-Boc]: 194.0781; found: 194.0777.

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