Asymmetric ~([2,3])-Wittig Rearrangement of Oxygenated Allyl Benzyl Ethersin the Presence of a Chiral di-tBu-bis(oxazoline) Ligand: A Novel SyntheticApproach to THF Lignans

Maria Kitamura; Yoshimi Hirokawa; Naoyoshi Maezaki

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Asymmetric ~([2,3])-Wittig Rearrangement of Oxygenated Allyl Benzyl Ethersin the Presence of a Chiral di-tBu-bis(oxazoline) Ligand: A Novel SyntheticApproach to THF Lignans

机译：手性di-tBu-双（恶唑啉）配体存在下的氧化烯丙基苄基醚的不对称〜（[[2,3]）-Wittig重排：THF木质素的新型合成方法

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We have accomplished highlyenantioselective [2,3]-Wittig rearrange-ments of functionalized allyl benzylethers in the presence of a chiral di-tBu-bis(oxazoline) ligand. In variousoxygenated benzylic ethers, the reac-tions proceeded with excellent diaster-eo- and enantioselectivities, althoughthe presence of a methoxy substituent at the ortho-position on the benzylgroup drastically decreased the enan-tioselectivity. Conversely, o-ethyl and o-phenyl substituents had no significanteffect on the selectivity. We found thatthe C2-substituent of the allylic moietyplayed an important role in producinghigh enantioselectivity. Highly enantio-selective [2,3]-Wittig rearrangement inthe presence of catalytic amounts ofthe chiral ligands is also described.

机译：在手性二叔丁基-双（恶唑啉）配体的存在下，我们已经完成了功能化的烯丙基苄基醚的高对映选择性[2,3]-维蒂希重排。在各种氧化的苄基醚中，反应进行时具有极好的对映体和对映体选择性，尽管在苄基的邻位存在甲氧基取代基会大大降低对映体选择性。相反，邻乙基和邻苯基取代基对选择性没有显着影响。我们发现，烯丙基部分的C2-取代基在产生高对映选择性中起重要作用。还描述了在催化量的手性配体存在下的高度对映选择性[2,3]-维蒂希重排。

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《Chemistry: A European journal》 |2009年第38期|共7页
作者
Maria Kitamura; Yoshimi Hirokawa; Naoyoshi Maezaki;
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正文语种 eng
中图分类应用化学;
关键词
Wittig rearrangement; asymmetric synthesis; externalchiral ligands; lignans; stereoselec-tivity;

机译：维蒂希重排;不对称合成;外手性配体;木脂素;立体选择性;

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1. Asymmetric ~([2,3])-Wittig Rearrangement of Oxygenated Allyl Benzyl Ethersin the Presence of a Chiral di-tBu-bis(oxazoline) Ligand: A Novel SyntheticApproach to THF Lignans [J] . Maria Kitamura, Yoshimi Hirokawa, Naoyoshi Maezaki Chemistry: A European journal . 2009,第38期

机译：手性di-tBu-双（恶唑啉）配体存在下的氧化烯丙基苄基醚的不对称〜（[[2,3]）-Wittig重排：THF木质素的新型合成方法
2. Highly enantioselective [2,3]-Wittig rearrangement of functionalized allyl benzyl ethers: a novel approach to lignan synthesis [J] . Hirokawa Y, Kitamura M, Maezaki N Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2008,第10期

机译：高度对映选择性[2,3] -Wittig重排的功能化的烯丙基苄醚：木脂素合成的新方法
3. Sparteine-Mediated Enantioselective [2,3]-Wittig Rearrangement of Allyl ortho-Substituted Benzyl Ethers and ortho-Substituted Benzyl Prenyl Ethers [J] . Takeshi Kawasaki, Tetsutaro Kimachi Tetrahedron . 1999,第22期

机译：Sparteine介导的烯丙基邻位取代的苄基醚和邻位取代的苄基戊烯基醚的对映选择性[2,3] -Wittig重排
4. A Chiral π–Cu(II) Complex-catalyzed 1,3 or 3,3 O-to-C Rearrangements of Allyl/Benzyl Naphthyl Ethers [C] . Lu Yao, Kazuaki Ishihara 日本化学会春季年会講演予稿集 . 2018

机译：手性π-Cu（II）复合催化1,3或3,3 O-TO-C的烯丙基/苄基萘基醚重排液
5. The Z-selective [2,3] Wittig rearrangement of secondary allylic alpha-stannyl ethers, chiral alpha-alkoxy stannanes, and progress toward the enantiospecific total synthesis of (+)-mycotrieninol I. [D] . Giamis, Anthony Martin. 2003

机译：仲烯丙基α-锡烷基醚，手性α-烷氧基锡烷的Z选择性[2,3] Wittig重排，并向（+）-霉三烯醇I的对映体总合成进展。
6. SYNTHESIS OF CHIRAL PYRIDINE BIS(OXAZOLINE) LIGANDS FOR NICKEL-CATALYZED ASYMMETRIC NEGISHI CROSS-COUPLINGS OF SECONDARY ALLYLIC CHLORIDES WITH ALKYLZINCS: 26-BIS(4S)-45-DIHYDRO-4-(2-PHENYLETHYL)-2-OXAZOLYL-PYRIDINE [O] . Sha Lou, Gregory C. Fu -1

机译：手性吡啶合成双（恶唑啉）的配体的镍 - 催化的不对称Negishi交叉联轴器sECONDaRY烯丙基氯化物WITH aLKYLZINCs作者：26-双（4s）-45-二氢-4-（2-苯乙基）-2-恶唑基吡啶
7. Asymmetric 2, 3-Wittig Rearrangement Induced by a Chiral Carbanion Whose Chirality Was Transferred from an Epoxide [O] . -1

机译：不对称2,3 -wittig被手性碳的细胞诱导，其性儿童从环氧化物转移

Asymmetric ~([2,3])-Wittig Rearrangement of Oxygenated Allyl Benzyl Ethersin the Presence of a Chiral di-tBu-bis(oxazoline) Ligand: A Novel SyntheticApproach to THF Lignans

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