Practical preparation of 4(R)-allylazetidinones and 4(R)-(1-methylallyl)azetidinones

Fliri, Hans; Mak, Ching-Pong

doi:10.1021/jo00219a003

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1989

2022

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Cited by 51 publications

(2 citation statements)

References 2 publications

(6 reference statements)

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“…42 Hitherto, radical reactions have seldom been used to introduce a side chain on β-lactam rings. 43 Such modifications have relied extensively on ionic processes. The present approach thus nicely complements existing methods.…”

Section: Account Syn Lettmentioning

confidence: 99%

The Xanthate Route to Amines, Anilines, and Other Nitrogen Compounds. A Brief Account

Quiclet‐Sire

Zard

2016

Synlett

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Section: Account Syn Lettmentioning

confidence: 99%

The Xanthate Route to Amines, Anilines, and Other Nitrogen Compounds. A Brief Account

Quiclet‐Sire

Zard

2016

Synlett

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“…Scheme 2. Reagents: i, PhCH,OH, Ti(OPr'),, 80°C, 2h; ii, Bu,NF, AcOH THF, O°C, 30 min; iii, [H,], 10% Pd-C/EtOH, room temp., 10 min; iv, m-CPBA/CH,Cl,, O'C, 1 h; v, Bu'Me,SiOC(=CH,)-C(=N,)CO,CH,Ph(7), cat. ZnI,, dry MeCN, room temp., 15 min.…”

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confidence: 99%

Chemistry of O-silylated ketene acetals: a synthesis of β-lactam antibiotics

Kita¹,

Tamura²,

Shibata³

et al. 1989

J. Chem. Soc., Perkin Trans. 1

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Preparation of 1-Hydroxycyclopentanecarboxylic Acid Derivatives from a Chiral Equivalent of Glycolic Acid

et al. 1999

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The stereoselective preparation of 1‐hydroxycyclopentanecarboxylic acid derivatives is reported. The key reaction is either a radical cyclization or a radical annulation mediated by the transfer of a phenylseleno group. The radical precursors are easily synthesized by two consecutive enolate alkylations. Excellent stereochemical control for the quaternary C(1) stereogenic center has been achieved.

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Practical preparation of 4(R)-allylazetidinones and 4(R)-(1-methylallyl)azetidinones

Cited by 51 publications

References 2 publications

The Xanthate Route to Amines, Anilines, and Other Nitrogen Compounds. A Brief Account

The Xanthate Route to Amines, Anilines, and Other Nitrogen Compounds. A Brief Account

Chemistry of O-silylated ketene acetals: a synthesis of β-lactam antibiotics

Preparation of 1-Hydroxycyclopentanecarboxylic Acid Derivatives from a Chiral Equivalent of Glycolic Acid

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