Asymmetric Organocatalytic Synthesis of trans-3,4-Disubstituted Isochromanones via an Intramolecular Aldol Reaction

被引：7

作者：

Fronert, Jeanne ^{[1
]}

Bisschops, Tom ^{[1
]}

Cassens-Sasse, Elisa ^{[1
]}

Atodiresei, Iuliana ^{[1
]}

Enders, Dieter ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 12期

关键词：

organocatalysis; aldol reaction; asymmetric synthesis; dihydroisocoumarin; enamine activation; POLYKETIDE METABOLITES; TRANSITION-STATES;

D O I：

10.1055/s-0033-1338742

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereo- and enantioselective synthesis of 3-acetyl-4-hydroxyisochroman-1-ones via an intramolecular trans-selective aldol reaction employing proline-type organocatalysts is described. Good yields (64-88%) and high stereoselectivities (87 to >95% de, 84-99% ee) are obtained, thus potentially enabling, for example, a new direct entry to carbazolelactone alkaloid natural products.

引用

页码：1708 / 1712

页数：5

共 37 条

[1] METABOLITES OF LASIODIPLODIA-THEOBROMAE [J].

ALDRIDGE, DC ;

GALT, S ;

GILES, D ;

TURNER, WB .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (09) :1623-&

[2]

[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650

[3] Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions [J].

Bahmanyar, S ;

Houk, KN ;

Martin, HJ ;

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2475-2479

[4] The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions [J].

Bahmanyar, S ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) :12911-12912

[5] Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity [J].

Bahmanyar, S ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11273-11283

[6]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[7] An Enantioselective Approach toward 3,4-Dihydroisocoumarin through the Bromocyclization of Styrene-type Carboxylic Acids [J].

Chen, Jie ;

Zhou, Ling ;

Tan, Chong Kiat ;

Yeung, Ying-Yeung .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (02) :999-1009

[8] A Catalytic Asymmetric Reaction Involving Enolizable Anhydrides [J].

Cornaggia, Claudio ;

Manoni, Francesco ;

Torrente, Esther ;

Tallon, Sean ;

Connon, Stephen J. .

ORGANIC LETTERS, 2012, 14 (07) :1850-1853

[9] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[10] TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS .6. NEW TYPE OF ASYMMETRIC CYCLIZATION TO OPTICALLY ACTIVE STEROID CD PARTIAL STRUCTURES [J].

EDER, U ;

SAUER, G ;

WEICHERT, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) :496-&

← 1 2 3 4 →