Oxidative umpolung α-alkylation of ketones

O. Svetlana Shneider; Evgeni Pisarevsky; Peter Fristrup; Alex M. Szpilman

doi:10.1021/ol503384c

Oxidative umpolung α-alkylation of ketones

O. Svetlana Shneider
, Evgeni Pisarevsky
, Peter Fristrup
, Alex M. Szpilman

نتاج البحث: نشر في مجلة › مقالة › مراجعة النظراء

47 اقتباسات (Scopus)

ملخص

We disclose a hypervalent iodine mediated α-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The α-alkylated carbonyl products are formed in up to 93% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies.

اللغة الأصلية	الإنجليزيّة
الصفحات (من إلى)	282-285
عدد الصفحات	4
دورية	Organic Letters
مستوى الصوت	17
رقم الإصدار	2
المعرِّفات الرقمية للأشياء	https://doi.org/10.1021/ol503384c
حالة النشر	نُشِر - 16 يناير 2015
منشور خارجيًا	نعم

الوصول إلى المستند

10.1021/ol503384c

الملفات والروابط الأخرى

Link to publication in Scopus

قم بذكر هذا

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title = "Oxidative umpolung α-alkylation of ketones",

abstract = "We disclose a hypervalent iodine mediated α-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The α-alkylated carbonyl products are formed in up to 93\% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies.",

author = "Shneider, \{O. Svetlana\} and Evgeni Pisarevsky and Peter Fristrup and Szpilman, \{Alex M.\}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

month = jan,

day = "16",

doi = "10.1021/ol503384c",

language = "אנגלית",

volume = "17",

pages = "282--285",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Oxidative umpolung α-alkylation of ketones

AU - Shneider, O. Svetlana

AU - Pisarevsky, Evgeni

AU - Fristrup, Peter

AU - Szpilman, Alex M.

PY - 2015/1/16

Y1 - 2015/1/16

N2 - We disclose a hypervalent iodine mediated α-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The α-alkylated carbonyl products are formed in up to 93% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies.

AB - We disclose a hypervalent iodine mediated α-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The α-alkylated carbonyl products are formed in up to 93% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies.

UR - https://www.scopus.com/pages/publications/84921315267

U2 - 10.1021/ol503384c

DO - 10.1021/ol503384c

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AN - SCOPUS:84921315267

SN - 1523-7060

VL - 17

SP - 282

EP - 285

JO - Organic Letters

JF - Organic Letters

IS - 2

ER -

Oxidative umpolung α-alkylation of ketones

ملخص

الوصول إلى المستند

الملفات والروابط الأخرى

بصمة

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