Highly stereoselective addition of stannylcuprates to alkynones

被引：13

作者：

Nielsen, TE ^{[1
]}

de Dios, MAC ^{[1
]}

Tanner, D ^{[1
]}

机构：

[1] Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 21期

关键词：

D O I：

10.1021/jo0259008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of stannylcuprate reagents such as (Bu3Sn)(PhS)CuLi to alkynones has been found to proceed in high yield and with excellent stereoselectivity for the Z isomer of the product (>95%). The behavior of the stannylcuprates is thus very different from that of their "carbocuprate" counterparts such as Me2CuLi or Me2Cu(CN)Li-2 which are nonstereoselective. Furthermore, in contrast to the reactions of (R3Sn)(PhS)CuLi with the corresponding alkynoates, the presence of a proton source in the reaction medium has no effect on the stereos electivity of the reaction of alkynones.

引用

页码：7309 / 7313

页数：5

共 27 条

[1] THE STANNYL CUPRATION OF ACETYLENES AND THE REACTION OF THE INTERMEDIATE CUPRATES WITH ELECTROPHILES AS A SYNTHESIS OF SUBSTITUTED VINYLSTANNANES [J].

BARBERO, A ;

CUADRADO, P ;

FLEMING, I ;

GONZALEZ, AM ;

PULIDO, FJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (04) :351-353

[2] Regiospecific and stereoselective synthesis of functionalized and differently metalated alkenes by silyl- or stannylcupration of metalated acetylenes [J].

Cuadrado, P ;

González-Nogal, AM ;

Sánchez, A .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (06) :1961-1965

[3]

DEGL'INNOCENTI A, 1992, SYNLETT, P332

[4] THE SYNTHESIS OF ALPHA-BETA-UNSATURATED KETONES FROM BETA-SILYLENONES AND BETA-SILYLYNONES [J].

FLEMING, I ;

PERRY, DA .

TETRAHEDRON, 1981, 37 (23) :4027-4034

[5] A STEREOCONTROLLED SYNTHESIS OF (+/-)-1,6,7-TRIDEOXYFORSKOLIN [J].

HASHIMOTO, S ;

SONEGAWA, M ;

SAKATA, S ;

IKEGAMI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (01) :24-25

[6] Efficient assembly of the phomactin core via two different macrocyclization protocols [J].

Houghton, TJ ;

Choi, S ;

Rawal, VH .

ORGANIC LETTERS, 2001, 3 (23) :3615-3617

[7]

HOUSE HO, 1975, J ORG CHEM, V40, P1460, DOI 10.1021/jo00898a019

[8] Efficient synthesis of 2-mono- and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones [J].

Kel'in, AV ;

Gevorgyan, V .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :95-98

[9]

LIPSHUTZ BH, 1992, ORG REACTIONS, V41, P135, DOI [DOI 10.1002/0471264180.0R041.02, 10.1002/0471264180.or041.02]

[10]

MARINO JP, 1976, TETRAHEDRON LETT, P3245

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