(2R)-2-<2-(tert-Butyldimethylsiloxy)pyrrol-1-yl>-2-phenylethylbenzoate | 228098-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R)-2-<2-(tert-Butyldimethylsiloxy)pyrrol-1-yl>-2-phenylethylbenzoate
• 英文别名: [(2R)-2-[2-[tert-butyl(dimethyl)silyl]oxypyrrol-1-yl]-2-phenylethyl] benzoate
• CAS: 228098-63-3
• 化学式: C₂₅H₃₁NO₃Si
• 分子量: 421.612
• InChiKey: MZGNVGKLJJTGBV-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2-<2-(tert-Butyldimethylsiloxy)pyrrol-1-yl>-2-phenylethylbenzoate 在 palladium on activated charcoal sodium hydroxide 、 lithium aluminium tetrahydride 、 molecular sieve 、 氢气 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Yb(OTf)3-catalyzed Mannich-type reaction of a chiral non-racemic silyloxypyrrole

  摘要：

  A Yb(OTf)(3)-catalyzed Mannich-type reaction of the chiral non-racemic silyloxypyrrole 2 is described. The three-component (silyloxypyrrole, aldehyde and amine) reaction allowed the use of aromatic as well as aliphatic enolisable aldehydes. The erythro selectivity was proved by chemical correlation and X-ray analysis. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01055-8
• 作为产物：
  描述：

  (R)-1-(2-羟基-1-苯乙基)-1,5-二氢吡咯-2-酮 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成 (2R)-2-<2-(tert-Butyldimethylsiloxy)pyrrol-1-yl>-2-phenylethylbenzoate
  参考文献：
  名称：

  Asymmetric Routes Towards Polyfunctionalized Pyrrolidines: A Short Diastereoselective Synthesis of Polyhydroxylated Pyrrolidines and an Indolizidine

  摘要：

  从(R)-(-)-苯甘氨醇出发，通过8步反应制备了各种(2S,3S,4R)-2-[(1R)-1-羟基烷基]吡咯烷-3,4-二醇(11)，总收率13-20%。这种简洁的方法是基于手性硅氧基吡咯与醛的缩合，从而得到(R,R)-醛缩化合物，收率高且立体选择性高。顺式羟基化后还原和脱保护得到所需的三羟基吡咯烷。同样的策略已成功应用于8a-表斯温森碱的正式合成。

  DOI：

  10.1055/s-1999-3434

文献信息

• Highly Efficient Asymmetric Access to 1-Azaspiro[4.4]nonane Skeleton
  作者：Jacques Royer、Loïc Planas、Joëlle Pérard-Viret、Mohamed Selkti、Alain Thomas

  DOI：10.1055/s-2002-34232

  日期：——

  Vinylogous Mukaiyama aldol type reaction of chiral non-racemic silyloxypyrroles followed by acidic treatment affords an efficient asymmetric access to 1-azaspiro[4.4]nonanes in high diastereoisomeric excess (up to 79%).

  在酸性处理后，通过手性非消旋硅氧吡咯的Vinylogous Mukaiyama醛醇型反应，实现了1-氮杂螺[4.4]壬烷的高效不对称合成，其立体异构体过量高达79%。
• Ytterbium triflate-catalyzed reactions of imines with a chiral non-racemic silyloxypyrrole
  作者：Bruno Dudot、Jacques Royer、Mireille Sevrin、Pascal George

  DOI：10.1016/s0040-4039(00)00625-0

  日期：2000.6

  In the presence of a catalytic amount of ytterbium triflate the reactions of various aromatic imines with a chiral non-racemic silyloxypyrrole proceeded smoothly to afford the corresponding aldol-type adducts in go od yields and diastereoselectivities. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Asymmetric routes towards polyfunctionalized pyrrolidines: application to the synthesis of alkaloid analogues
  作者：Martial Toffano、Bruno Dudot、Anne Zaparucha、Jacques Royer、Mireille Sevrin、Pascal George、Angèle Chiaroni

  DOI：10.1016/s0957-4166(03)00592-5

  日期：2003.10

  The Mukaiyama aldol type condensation of t-butyldimethylsilyloxypyrrole 1b with methyl 2-formylbenzoate furnished the aldol adduct 9 with high yield and complete stereoselectivity. An erythro (anti) configuration was established (X-ray) in sharp contrast with the reaction of 1b with aliphatic aldehydes. Simple chemical transformations were used to transform 9 into original phthalidopyrrolidine compound analogous of bicuculline alkaloids. (C) 2003 Elsevier Ltd. All rights reserved.
• Yb(OTf)3-catalyzed Mannich-type reaction of a chiral non-racemic silyloxypyrrole
  作者：Bruno Dudot、Angèle Chiaroni、Jacques Royer

  DOI：10.1016/s0040-4039(00)01055-8

  日期：2000.8

  A Yb(OTf)(3)-catalyzed Mannich-type reaction of the chiral non-racemic silyloxypyrrole 2 is described. The three-component (silyloxypyrrole, aldehyde and amine) reaction allowed the use of aromatic as well as aliphatic enolisable aldehydes. The erythro selectivity was proved by chemical correlation and X-ray analysis. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Asymmetric Routes Towards Polyfunctionalized Pyrrolidines: A Short Diastereoselective Synthesis of Polyhydroxylated Pyrrolidines and an Indolizidine
  作者：Bruno Dudot、Laurent Micouin、Isabelle Baussanne、Jacques Royer

  DOI：10.1055/s-1999-3434

  日期：1999.4

  Various (2S,3S,4R)-2-[(1R)-1-hydroxyalkyl]pyrrolidine-3,4-diols (11) have been prepared in 8 steps and 13-20% overall yields starting from (R)-(-)-phenylglycinol. This concise approach is based on the condensation of a chiral silyloxypyrrole with aldehydes which gave the (R,R)-aldol compounds in good yields and high diastereoselectivities. The cis-hydroxylation followed by reduction and deprotection gave the desired trihydroxylated pyrrolidines. The same strategy has been successively applied to a formal synthesis of 8a-epi-swainsonine.

  从(R)-(-)-苯甘氨醇出发，通过8步反应制备了各种(2S,3S,4R)-2-[(1R)-1-羟基烷基]吡咯烷-3,4-二醇(11)，总收率13-20%。这种简洁的方法是基于手性硅氧基吡咯与醛的缩合，从而得到(R,R)-醛缩化合物，收率高且立体选择性高。顺式羟基化后还原和脱保护得到所需的三羟基吡咯烷。同样的策略已成功应用于8a-表斯温森碱的正式合成。