Reaction of the levoglucosenone Diels-Alder adducts with acetaldehyde under the McMurry conditions

被引：3

作者：

Faizullina, Lilia Kh ^{[1
]}

Tagirov, Artur R. ^{[1
]}

Salikhov, Shamil M. ^{[1
]}

Valeev, Farid A. ^{[1
]}

机构：

[1] Russian Acad Sci, Ufa Inst Chem, Ufa Fed Res Ctr, Ufa 450054, Russia

来源：

MENDELEEV COMMUNICATIONS | 2022年 / 32卷 / 01期

关键词：

levoglucosenone; Diels-Alder adducts; acetaldehyde; acetals; McMurry reaction; pinacol reaction; STEREOSELECTIVE SYNTHESIS; TITANIUM; CYCLOADDITION; DERIVATIVES; KETONES;

D O I：

10.1016/j.mencom.2022.01.032

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reactions of acetaldehyde with Diels-Alder adducts of levoglucosenone with butadiene, isoprene, and cyclohexadiene assisted by low-valence titanium afford products of acetaldehyde addition to the acetal center with opening of the 1,6-anhydro bridge. In the case of the cyclopentadiene adduct, the reaction gives the product of addition of the ethyl substituent to the acetal center while the 1,6-anhydro bridge remains unchanged.

引用

页码：100 / 102

页数：3

共 26 条

[11] CARBONYL-COUPLING REACTIONS USING LOW-VALENT TITANIUM [J].

MCMURRY, JE .

CHEMICAL REVIEWS, 1989, 89 (07) :1513-1524

[12] TITANIUM-INDUCED REDUCTIVE COUPLING OF CARBONYLS TO OLEFINS [J].

MCMURRY, JE ;

FLEMING, MP ;

KEES, KL ;

KREPSKI, LR .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (17) :3255-3266

[13] SYNTHESIS OF UNSYMMETRICAL OLEFINS BY TITANIUM(0) INDUCED MIXED CARBONYL COUPLING - SOME COMMENTS ON MECHANISM OF PINACOL REACTION [J].

MCMURRY, JE ;

KREPSKI, LR .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (24) :3929-3930

[14]

Miftakhov M. S., 1996, RUSS CHEM B+, V45, P2047

[15]

Miftakhov M.S., 1994, Russ. Chem. Rev, V63, P869, DOI DOI 10.1070/RC1994V063N10ABEH000123

[16]

MIFTAKHOV MS, 1994, MENDELEEV COMMUN, P45

[17] NEW ALDOL TYPE REACTION [J].

MUKAIYAMA, T ;

NARASAKA, K ;

BANNO, K .

CHEMISTRY LETTERS, 1973, (09) :1011-1014

[18] Exploring structural effects of levoglucosenone derived chiral auxiliaries in asymmetric Diels-Alder cycloadditions [J].

Sarotti, Ariel M. ;

Spanevello, Rolando A. ;

Duhayon, Carine ;

Tuchagues, Jean-Pierre ;

Suarez, Alejandra G. .

TETRAHEDRON, 2007, 63 (01) :241-251

[19]

Sarotti AM, 2012, CURR ORG SYNTH, V9, P439

[20] DFT calculations induced a regiochemical outcome revision of the Diels-Alder reaction between levoglucosenone and isoprene [J].

Sarotti, Ariel M. ;

Suarez, Alejandra G. ;

Spanevello, Rolando A. .

TETRAHEDRON LETTERS, 2011, 52 (24) :3116-3119

← 1 2 3 →