Aldol strategy: coordination of the lithium cation with an alkoxy substituent

S Masamune, JW Ellingboe…

Index: Masamune, Saturu; Ellingboe, John W.; Choy, William Journal of the American Chemical Society, 1982 , vol. 104, # 20 p. 5526 - 5528

Full Text: HTML

Citation Number: 103

Abstract

4 (Scheme 11) with a Z (0)-enolate (5)'proceeds through a Cram-type2 transition state (6)[with 5 approaching 4 from the.(re) face of 41 or (7)[with 5 approaching 4 from the p (si) face of 41.'Transition states 6 and 7 should provide the 2, 3-syn, 3, 4-anti, 4, 5-syn-3, 5- dihydroxy-2, 4-dimethylcar~ nyl derivative 8 and the corresponding 2, 3-syn, 3, 4-syn, 4, 5- syn derivative 9,'respectively. As the lithium cation coordinates more tightly with both ...

Related Articles:

Stereo-and regio-selective conversion of 1-trimethylsilylallylic alcohols into the silyl enol ethers catalyzed by butyllithium

[Kuwajima, Isao; Kato, Masahiro; Mori, Akio Tetrahedron Letters, 1980 , vol. 21, p. 2745 - 2748]

A stereoselective isomerization of allyl silyl ethers to (E)-or (Z)-silyl enol ethers using cationic iridium complexes

[Ohmura, Toshimichi; Shirai, Yasuo; Yamamoto, Yasunori; Miyaura, Norio Chemical Communications, 1998 , # 13 p. 1337 - 1338]

Regio-and stereoselective preparation of silyl enol ethers by alkylidenation of silyl esters

[Takai, Kazuhiko; Kataoka, Yasutaka; Okazoe, Takashi; Utimoto, Kiitiro Tetrahedron Letters, 1988 , vol. 29, # 9 p. 1065 - 1068]

Regio-and stereodefined synthesis of trimethylsilyl enol ethers resulted from the isomerization of α-trimethylsilyl ketones

[Matsuda, Isamu; Sato, Susumu; Hattori, Motoaki; Izumi, Yusuke Tetrahedron Letters, 1985 , vol. 26, # 27 p. 3215 - 3218]

More Articles...