Exploring modular domino reactions: Competing processes based on the nature of the angular substituent

被引：9

作者：

Elkhayat, Zobida ^{[1
]}

Safir, Imad ^{[1
]}

Retailleau, Pascal ^{[1
]}

Arseniyadis, Simeon ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 23期

关键词：

D O I：

10.1021/ol7021643

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The octaline diol system 6 was found to undergo an interesting set of reactions upon treatment with Phl(OAc)(2), leading, in a single synthetic operation, to complex oxygen heterocycles. Experimental evidence supports an intramolecular hetero[4 + 2 + 2] adduct that has heretofore never been observed, which completely dominates the hetero[4 + 2] path in several cases. The domino protocol can be biased one way or another depending on both the nature of the;pi-system and the length of the methylene spacer at the angular position.

引用

页码：4841 / 4844

页数：4

共 23 条

[1] CATALYTIC BEHAVIOR OF SOME ZIEGLER-NATTA CATALYSTS IN NORBORNADIENE-BUTADIENE CODIMERIZATION [J].

CARBONAR.A ;

CAMBISI, F ;

DALLASTA, G .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (10) :1443-&

[2] Enantioselective total synthesis of 1-epi-pathylactone A [J].

Chanu, Angeline ;

Safir, Imad ;

Basak, Ramkrishna ;

Chiaroni, Angele ;

Arseniyadis, Simeon .

ORGANIC LETTERS, 2007, 9 (07) :1351-1354

[3]

Chanu A, 2007, EUR J ORG CHEM, V2007, P4305

[4]

Criegee R, 1939, LIEBIGS ANN CHEM, V541, P218

[5] An efficient one-pot approach to bridged bicyclic ring-systems through consecutive hetero-domino transformations: A mechanistic rationale and further rearrangements [J].

Finet, L ;

Lena, JIC ;

Kaoudi, T ;

Birlirakis, N ;

Arseniyadis, S .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (16) :3813-3820

[6] Enantioselective synthesis of a Wieland-Miescher ketone bearing an angular hydroxymethyl group [J].

Hanselmann, R ;

Benn, M .

SYNTHETIC COMMUNICATIONS, 1996, 26 (05) :945-961

[7] PERICYCLIC REACTION TRANSITION-STATES - PASSIONS AND PUNCTILIOS, 1935-1995 [J].

HOUK, KN ;

GONZALEZ, J ;

LI, Y .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (02) :81-90

[8] First synthesis of the A/B ring of ouabain [J].

Jung, ME ;

Piizzi, G .

ORGANIC LETTERS, 2003, 5 (02) :137-140

[9] Synthetic approach to the AB ring system of ouabain [J].

Jung, ME ;

Piizzi, G .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2572-2582

[10] Cobalt-catalyzed [4+2+2] cycloadditions of bicyclo[2.2.2]octadienes [J].

Kiattansakul, R ;

Snyder, JK .

TETRAHEDRON LETTERS, 1999, 40 (06) :1079-1082

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