Syntheses and reactions of multifunctional carbanions "ynolate anions"

被引:25
作者
Shindo, M [1 ]
机构
[1] Univ Tokushima, Inst Med Resources, Tokushima 7708505, Japan
关键词
ynolate; carbanion; olefination; beta-lactone; beta-lactam; tandem reaction; cycloaddition; ketene; dianion;
D O I
10.5059/yukigoseikyokaishi.58.1155
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ynolates are carbanions having a triple bond in place of the double bond in enolate anions. Ynolates are ketene anion equivalents, thus ynolates introduce a ketene unit into substrates and the resulting products possess high reactivity. This allows ynolates to undergo unique reaction sequences. For the past 20 years, several methods for the generation of ynolates and their reactions have been developed. Recently, we have developed a highly efficient method for their generation and new rections such as olefination, tandem [2+2] cycloaddition-Dieckmann condensation, syntheses of beta -lactams. In this review, an overview of the syntheses and the reactions of ynolates, especially focusing our recent results, are described.
引用
收藏
页码:1155 / 1166
页数:12
相关论文
共 56 条
[1]   NOVEL SYNTHESES OF 3-METHYLENE-AZETIDIN-2-ONE DERIVATIVES AND RELATED SYSTEMS [J].
ADLINGTON, RM ;
BARRETT, AGM ;
QUAYLE, P ;
WALKER, A ;
BETTS, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (09) :404-405
[2]   The development and use of ketene equivalents in [4+2] cycloadditions for organic synthesis [J].
Aggarwal, VK ;
Ali, A ;
Coogan, MP .
TETRAHEDRON, 1999, 55 (02) :293-312
[3]   Reaction of ynolate anions derived from silylketenes with electrophiles: A facile preparation of silyl ynol ethers and functionalized silylketenes [J].
Akai, S ;
Kitagaki, S ;
Naka, T ;
Yamamoto, K ;
Tsuzuki, Y ;
Matsumoto, K ;
Kita, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (14) :1705-1709
[4]   SYNTHESIS OF BETA-LACTAMS FROM IMINES AND 1-LITHIO-OXY-2-PHENYLACETYLENE [J].
BARRETT, AGM ;
QUAYLE, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (09) :2193-2196
[5]   FLASH PHOTOLYTIC GENERATION AND STUDY OF YNOLATE IONS AND THE CORRESPONDING KETENES IN AQUEOUS-SOLUTION [J].
CHIANG, Y ;
KRESGE, AJ ;
POPIK, VV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (36) :9165-9171
[6]   2-methylcyclopentane-1,3-dione: An efficient synthon for the synthesis of (+/-)-alpha-cuparenone. [J].
Cossy, J ;
Gille, B ;
BouzBouz, S ;
Bellosta, V .
TETRAHEDRON LETTERS, 1997, 38 (23) :4069-4070
[7]   TOTAL SYNTHESIS OF DAN SHEN DITERPENOID QUINONES [J].
DANHEISER, RL ;
CASEBIER, DS ;
LOEBACH, JL .
TETRAHEDRON LETTERS, 1992, 33 (09) :1149-1152
[8]   TOTAL SYNTHESIS OF AEGYPTINONE-A AND AEGYPTINONE-B [J].
DANHEISER, RL ;
CASEBIER, DS ;
HUBOUX, AH .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4844-4848
[9]   TOTAL SYNTHESIS OF MYCOPHENOLIC-ACID [J].
DANHEISER, RL ;
GEE, SK ;
PEREZ, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (04) :806-810
[10]   TOTAL SYNTHESIS OF THE HOST DEFENSE STIMULANT MAESANIN [J].
DANHEISER, RL ;
CHA, DD .
TETRAHEDRON LETTERS, 1990, 31 (11) :1527-1530