Asymmetric addition of allylic stannanes to aldehydes catalyzed by BINAP•Ag(I) complex

被引：40

作者：

Yanagisawa, A ^{[1
]}

Nakashima, H ^{[1
]}

Nakatsuka, Y ^{[1
]}

Ishiba, A ^{[1
]}

Yamamoto, H ^{[1
]}

机构：

[1] Nagoya Univ, CREST, Japan Sci & Technol Corp, JST,Grad Sch Engn, Nagoya, Aichi 4648603, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2001年 / 74卷 / 06期

关键词：

D O I：

10.1246/bcsj.74.1129

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic asymmetric allylation of aldehydes with allylic trialkylstannanes was achieved with BINAP . AgOTf complex as catalyst. The chiral silver(I) catalyst was readily prepared by stirring an equimolar mixture of BINAP and silver(I) triflate in THF at room temperature. The allylation of a variety of aromatic and alpha,beta -unsaturated aldehydes resulted in high yields and remarkable enantioselectivities. Addition of gamma -substituted allylstannanes such as 2-butenyltributylstannane and trialkyl-2,4-pentadienylstannanes exclusively gave gamma -adducts. High anti-selectivity was also obtained in the reaction with 2-butenyltributylstannane, irrespective of the configuration at the double bond.

引用

页码：1129 / 1137

页数：9

共 76 条

[51]

PAZSANDOVAL MD, 1981, J ORGANOMET CHEM, V219, P81

[52] CHIRAL SYNTHESIS VIA ORGANOBORANES .36. EXCEPTIONALLY ENANTIOSELECTIVE ALLYLBORATIONS OF REPRESENTATIVE HETEROCYCLIC ALDEHYDES AT -100-DEGREES-C UNDER SALT-FREE CONDITIONS [J].

RACHERLA, US ;

LIAO, Y ;

BROWN, HC .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6614-6617

[53] ENANTIOSELECTIVE SYNTHESES WITH TITANIUM-CARBOHYDRATE COMPLEXES .1. ENANTIOSELECTIVE ALLYLATION OF CARBONYL-COMPOUNDS WITH TITANIUM-CARBOHYDRATE COMPLEXES [J].

RIEDIKER, M ;

DUTHALER, RO .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (04) :494-495

[54]

Roush W.R., 1991, Comprehensive Organic Synthesis, V2, P1, DOI DOI 10.1016/B978-0-08-052349-1.00023-8

[55] ASYMMETRIC-SYNTHESIS USING DIISOPROPYL TARTRATE MODIFIED (E)-CROTYLBORONATES AND (Z)-CROTYLBORONATES - PREPARATION OF THE CHIRAL CROTYLBORONATES AND REACTIONS WITH ACHIRAL ALDEHYDES [J].

ROUSH, WR ;

ANDO, K ;

POWERS, DB ;

PALKOWITZ, AD ;

HALTERMAN, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6339-6348

[56]

Santelli M., 1996, LEWIS ACIDS SELECTIV, P91

[57] OPTICALLY-ACTIVE ALCOHOLS FROM 1,3-DIOXAN-4-ONES - A PRACTICAL VERSION OF ENANTIOSELECTIVE SYNTHESIS WITH NUCLEOPHILIC-SUBSTITUTION AT ACETAL CENTERS [J].

SEEBACH, D ;

IMWINKELRIED, R ;

STUCKY, G .

HELVETICA CHIMICA ACTA, 1987, 70 (02) :448-464

[58] ETA-5-PENTADIENYLTRICARBONYLMANGANESE, AN OPEN ANALOG OF CYMANTRENE [J].

SEYFERTH, D ;

GOLDMAN, EW ;

PORNET, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 208 (02) :189-193

[59] A USEFUL DIENEMETHYLATION AGENT - 2,4-PENTADIENYLTRIMETHYLSILANE [J].

SEYFERTH, D ;

PORNET, J ;

WEINSTEIN, RM .

ORGANOMETALLICS, 1982, 1 (12) :1651-1658

[60] (2,4-PENTADIENYL)TRIMETHYLSILANE - A USEFUL PENTADIENYLATION REAGENT [J].

SEYFERTH, D ;

PORNET, J .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (09) :1721-1722

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