The 2-(N,N-dimethylamino)phenylsulfinyl group as an efficient chiral auxiliary in intramolecular Heck reactions

被引：26

作者：

Buezo, ND ^{[1
]}

Mancheño, OG ^{[1
]}

Carretero, JC ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, Madrid 28049, Spain

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 10期

关键词：

D O I：

10.1021/ol005779w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The synthesis, reactivity, and stereochemical behavior of differently substituted iodoalkenyl alpha,beta-unsaturated sulfoxides in intramolecular Heck reaction is described. Particularly, the 2-(N,N dimethylamino)phenylsulfinyl group is demonstrated to be an effective chiral auxiliary for the intramolecular Heck reaction of 2-iodo-1,6-(or 1,7)dienes. A desulfinylation sequence removes the auxiliary and yields cyclic compounds of high enantiopurity.

引用

页码：1451 / 1454

页数：4

共 29 条

[11] (S)-Proline-derived new chiral ligands with phosphino, organosulfur or organoselenenyl functionality as an enantiocontrollable coordinating element [J].

Hiroi, K ;

Suzuki, Y ;

Abe, I .

TETRAHEDRON-ASYMMETRY, 1999, 10 (06) :1173-1188

[12] Synthetic studies on (+)-wortmannin. An asymmetric construction of an allylic quaternary carbon center by a Heck reaction. [J].

Honzawa, S ;

Mizutani, T ;

Shibasaki, M .

TETRAHEDRON LETTERS, 1999, 40 (02) :311-314

[13]

Lacote E, 1998, ANGEW CHEM INT EDIT, V37, P2116, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2116::AID-ANIE2116>3.0.CO

[14]

2-L

[15] Catalytic asymmetric synthesis of either enantiomer of the Calabar alkaloids physostigmine and physovenine [J].

Matsuura, T ;

Overman, LE ;

Poon, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6500-6503

[16] PALLADIUM-CATALYZED POLYCYCLIZATIONS .4. PALLADIUM-CATALYZED POLYCYCLIZATIONS OF SUBSTITUTED DIENYNES - STEREOSELECTIVE ROUTES TO HIGHLY COMPLEX POLYCYCLES [J].

MEYER, FE ;

HENNIGES, H ;

DEMEIJERE, A .

TETRAHEDRON LETTERS, 1992, 33 (52) :8039-8042

[17] Silver salt effects on an asymmetric Heck reaction. Catalytic asymmetric total synthesis of (+)-xestoquinone. [J].

Miyazaki, F ;

Uotsu, K ;

Shibasaki, M .

TETRAHEDRON, 1998, 54 (43) :13073-13078

[18] ARYLATION OF OLEFIN WITH ARYL IODIDE CATALYZED BY PALLADIUM [J].

MIZOROKI, T ;

MORI, K ;

OZAKI, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1971, 44 (02) :581-+

[19]

Namyslo JC, 1999, SYNLETT, P804

[20] A NEW DESULFONYLATION OF ALPHA,BETA-UNSATURATED SULFONES VIA CONJUGATE ADDITION OF TRIBUTYLSTANNYL-LITHIUM [J].

OCHIAI, M ;

UKITA, T ;

FUJITA, E .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (11) :619-620

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