Enantioselective Reaction of Diketene to Aldehydes Promoted by Chiral Titanium Complexes

手性钛配合物促进双烯酮与醛的对映选择性反应

• 批准号: 06640690
• 负责人: HAYASHI Masahiko
• 金额: $ 1.54万
• 依托单位: Yamaguchi University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (C)
• 财政年份: 1994
• 资助国家: 日本
• 起止时间: 1994 至 1995
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-06640690/
• 关键词: titanum catalyst; Schiff base; diketene; optically active; enantioselectivity; 不斉; キラル; チタン; 触媒; エナンチオ選択的反応

Optically Active 5-hydroxy-3-oxoesters can be converted into 6-substituted 4-hydroxy lactones which are common structural components of compactin and mevinolin known as inhibitors of 3-hydroxy-3-methylglutaryl Coenzyme A (HMG-CoA) reductase. W e recently succeeded in the highly efficient preparation of optically active 5-hydroxy-3-oxoesters by enantioselective reaction of diketene with aldehydes promoted by novel chiral Schiff basetitanium alkoxide complexes. This new procedure provides an efficient method for the synthesis of optically active 5-hydroxy-3-oxoesters in up to 92% enantiomeric excess (ee).

光学活性的5-羟基-3-氧代酯可以转化为6-取代的4-羟基内酯，其是已知为3-羟基-3-甲基戊二酰辅酶A（HMG-CoA）还原酶抑制剂的康伐他汀和美维诺林的常见结构组分。我们最近成功地通过新型手性Schiff碱钛醇盐配合物促进的双烯酮与醛的不对称反应高效制备了光学活性的5-羟基-3-氧代酯。这种新方法为合成光学活性5-羟基-3-氧代酯提供了一种有效的方法，对映体过量（ee）高达92%。

项目成果

M.Hayashi: "Novel Enantioselective Reaction of Diketene with Some Aldehydes Promoted by Chiral Schiff Base-Titanium Alkoxide Complex." J.Chem.Soc,.Chem.Commun.341-342 (1994)

M.Hayashi：“手性席夫碱-钛醇盐络合物促进双烯酮与某些醛的新型对映选择性反应。”

M.Hayashi: "Reduction of alpha-Trialkylsiloxy Nitriles with Diisobutylaluminium Hydride (DIBAH) : A Facile Preparation of alpha-Trialkylsiloxy Aldehydes and their Derivatives" Tetrahedron. 50. 2821-2830 (1994)

M.Hayashi：“用二异丁基氢化铝 (DIBAH) 还原 α-三烷基硅氧基腈：α-三烷基硅氧基醛及其衍生物的简便制备”四面体。

M.Hayashi: "Highly Efficient Preparation of Optically Active 5-Hydroxy-3-oxoesters by Enantioselective Reaction of Diketene with Aldehydes Promoted by Novel Chiral Schiff Base-Titanium Alkoxide Complexes" Tetrahedron Asymmetry. 6. 1833-1836 (1995)

M.Hayashi：“新型手性希夫碱-钛醇盐配合物促进双烯酮与醛的对映选择性反应高效制备光学活性 5-羟基-3-氧代酯”四面体不对称性。

M. Hayashi: "Novel Enantioselective Reaction of Diketene with Aldehydes Promoted by Chiral Schiff Base-Titanium Alkoxide Complex" J. Chem. Soc., Chem. Commun.341-342 (1994)

M. Hayashi：“手性希夫碱-钛醇盐复合物促进双烯酮与醛的新型对映选择性反应”J. Chem。

林 昌彦: "光学活性シッフ塩基-チタンアルコキシド触媒を用いた不斉炭素-炭素結合生成反応" 有機合成化学協会誌. 52. 488-497 (1994)

Masahiko Hayashi：“使用光学活性希夫碱-钛醇盐催化剂的不对称碳-碳键形成反应”合成有机化学学会杂志 52. 488-497 (1994)。