Titanocene(II)-Promoted Stereoselective Alkenylation Utilizing (<i>Z</i>)-Alkenyl Sulfones

Ogata, Akitoshi; Nemoto, Masami; Kobayashi, Kenji; Tsubouchi, and Akira; Takeda, Takeshi

doi:10.1021/jo070149u

Cited by 15 publications

(1 citation statement)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[38] This compound was obtained from 2-bromoprop-1-ene (1x)i n8 9% yield. Yellow oil; (E)-1,3-Diphenylprop-2-en-1-ol [(E)-4 y] [39] and (Z)-1,3-Diphenylprop-2-en-1-ol [(Z)-4 y]. [40] These compounds were obtained from (E)-(2-bromovinyl)benzene (1y)i n7 6% yield with an E/Z ratio of 56:44.…”

Section: Grignardr Eagent ½Ml ð1þmentioning

confidence: 99%

Grignard Reactions in Cyclopentyl Methyl Ether

et al. 2016

View full text Add to dashboard Cite

We undertook asystematic study of Grignard reactions using cyclopentyl methyle ther (CPME)a sareaction solvent. Diisobutylaluminumh ydride was found to be the most appropriate activator of magnesium and an umber of Grignard reagents could be prepared as homogeneous or heterogeneouss olutions in CPME. The CPME used in the Grignard reactionw as efficientlyr ecycledw ithout affecting the reactiony ield of the second experiment.G C-MS analysis of the recovereds olventr evealed that CPME was stable under the Grignardc onditions. Some of the Grignard reagents in CPME were stable for at least several months and therefore these solutions could replace existing commercial reagents.T ramadol hydrochloride, an analgesic that is used worldwide, and tamoxifen, an anti-estrogenic drug for estrogen-receptor-positive breast cancer were synthesized using Grignard reactions in CPME.

show abstract

Section: Grignardr Eagent ½Ml ð1þmentioning

confidence: 99%

Grignard Reactions in Cyclopentyl Methyl Ether

et al. 2016

View full text Add to dashboard Cite

show abstract

Chemoselective and Direct Functionalization of Methyl Benzyl Ethers and Unsymmetrical Dibenzyl Ethers by Using Iron Trichloride

Sawama

Goto

Nagata

et al. 2014

Chemistry A European J

View full text Add to dashboard Cite

Methyl and benzyl ethers are widely utilized as protected alcohols due to their chemical stability, such as the low reactivity of the methoxy and benzyloxy groups as leaving groups under nucleophilic conditions. We have established the direct azidation of chemically stable methyl and benzyl ethers derived from secondary and tertiary benzyl alcohols. The present azidation chemoselectively proceeds at the secondary or tertiary benzylic positions of methyl benzyl ethers or unsymmetrical dibenzyl ethers and is also applicable to direct allylation, alkynylation, and cyanation reactions, as well as the azidation. The present methodologies provide not only a novel chemoselectivity but also the advantage of shortened synthetic steps, due to the direct process without the deprotection of the methyl and benzyl ethers.

show abstract

Titanocene(II)‐Promoted Stereoselective Alkenylation Utilizing (Z)‐Alkenyl Sulfones.

et al. 2007

View full text Add to dashboard Cite

Titanocene(II)-Promoted Stereoselective Alkenylation Utilizing (Z)-Alkenyl Sulfones. -Ti-mediated treatment of (Z)-alkenyl sulfones with aldehydes, ketones, or alkynes offers a new method to prepare (E)-configurated allylic alcohols and conjugated dienes. -(OGATA, A.; NEMOTO, M.; KOBAYASHI, K.; TSUBOUCHI, A.; TAKEDA*, T.; J. Org. Chem. 72 (2007) 10, 3816-3822; Dep. Appl. Chem., Grad. Sch. Eng., Tokyo Univ. Agric. Technol., Koganei, Tokyo 184, Japan; Eng.) -Jannicke 37-053

show abstract

Titanocene(II)-Promoted Stereoselective Alkenylation Utilizing (Z)-Alkenyl Sulfones

Cited by 15 publications

References 54 publications

Grignard Reactions in Cyclopentyl Methyl Ether

Grignard Reactions in Cyclopentyl Methyl Ether

Chemoselective and Direct Functionalization of Methyl Benzyl Ethers and Unsymmetrical Dibenzyl Ethers by Using Iron Trichloride

Titanocene(II)‐Promoted Stereoselective Alkenylation Utilizing (Z)‐Alkenyl Sulfones.

Contact Info

Product

Resources

About