Diastereoselective synthesis of (1S,2S,3R,6S) 3-chloro-3-methyl-6-isopropenyl-1,2-cyclohexanediol via Prins reaction induced by zinc and trimethylsilyl chloride

DOI: 10.1016/0040-4020(96)00167-6

Source and publish data:

Tetrahedron p. 4645 - 4658 (1996)

Update date:2022-07-29

Topics:

Authors:

Marty, Maurus

Stoeckli-Evans, Helen

Neier, Reinhard

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1016/0040-4020(96)00167-6

While attempting to synthesize a potential inhibitor of the biosynthesis step of formation of PBG, a novel catalytic system inducing the Prins reaction was discovered. Treatment of epoxy geranial with Zn and trimethylsilyl chloride gave (1S,2S,3R,6S) 3-Chloro-3-methyl-6-isopropenyl-1,2-cyclohexanediol in high diastereoselectivity.

Full text of DOI:10.1016/0040-4020(96)00167-6

Products guided by the article

Product name:Oxiranecarboxaldehyde, 3-methyl-3-(3-pentenyl)-, [2R-[2alpha,3beta(Z)]]- (9CI)

Cas No:176695-89-9

R&D Labs maybe for 176695-89-9

Hunan Haili Chemical Industry Co.,Ltd.

Contact:+86-731-85521860

Address:No.251, 2nd Section, Furong Road, Changsha,Hunan,China
Hangzhou Mole's Science & Technology Co.,Ltd.(expird)

Contact:+86-571-56880228

Address:15F Guodu development Building, NO.182 Zhaohui Road
Wuhan Shangrisyn chemicals Technology Co.,Ltd(expird)

Contact:+86-027-84466317 __ +86-15387123698

Address:wuhan - china
Wuxi Olite Chemical Co., Ltd.

Contact:86-510-82853889

Address:Rm.3732, No.18-2,Yonghe Rd.,Wuxi,Jiangsu,214023,China
JiangXi Hong Run Chemical Co., Ltd

Contact:+86-0791-88521351

Address:XingHuo industrial zone in YongXiu county

Relevant to this article

IODINATION OF PHENOLS USING CHLORAMINE T AND SODIUM IODIDE

Doi:10.1016/S0040-4039(00)94774-9
(1985)
Chemoselectivity in the rhodium(II) acetate catalysed decomposition of α-diazo-β-keto-γ,δ-alkenyl-δ-aryl compounds: Aromatic C-H insertion reaction or Wolff rearrangement-electrocyclization

Doi:10.1016/0040-4020(96)00581-9
(1996)
Cycloreversion of 1-(1-Naphthyl)-5-phenylbicyclo[3.2.0]hept-6-ene to 1-(1-Naphthyl)-4-phenyl-1,3-cycloheptadiene by Triplet Sensitization and Direct Irradiation

Doi:10.1246/bcsj.69.1313
(1996)
Antihyperglycemic activities of cryptolepine analogues: An ethnobotanical lead structure isolated from Cryptolepis sanguinolenta

Doi:10.1021/jm970735n
(1998)
Biomimetic synthesis of the microbial elicitor syringolide 2

Doi:10.1016/0040-4039(96)00611-9
(1996)
2-(Trimethylsilyl)phenyl Trimethylsilyl Ethers as Stable and Readily Accessible Benzyne Precursors

Doi:10.1021/acs.joc.7b00238
(2017)

Article Doi