Chirality transferring [3,3] sigmatropic rearrangement of (1-Acyloxy-2-alkenyl)trianlkylsilane synthesis of optically active vinylsilane-containing alpha-amino acid.

Chirality transferring [3,3] sigmatropic rearrangement of (1-Acyloxy-2-alkenyl)trianlkylsilane synthesis of optically active vinylsilane-containing alpha-amino acid.
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(1-酰氧基-2-烯基)三烷基硅烷的手性转移[3,3]σ重排合成含光学活性乙烯基硅烷的α-氨基酸。

DOI:
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发表时间:
2001
期刊:
影响因子:
2
通讯作者:
Y. Ohfune
Y. Ohfune
中科院分区:
化学4区
文献类型:
--
作者:
Kazuhiko Sakaguchi;Hiroyuki Suzuki;Y. Ohfune

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通过α-酰氧基硅烷1的酯-烯式Claisen重排反应作为关键步骤,以光学活性的形式合成了含有乙烯基硅烷的α-氨基酸和α,α-二取代的α-氨基酸2,其中α-酰氧基-TBDMS的手性完全转移到重排产物上。
A vinylsilane-containing alpha-amino acid and alpha,alpha-disubstituted alpha-amino acid 2 having two contiguous asymmetric carbon centers at their alpha and beta positions were synthesized in an optically active form by ester-enolate Claisen rearrangement of the alpha-acyloxysilane 1 as the key step, where the chirality of an alpha-acyloxy-TBDMS group was completely transferred to the rearranged product.
DOI: 10.1126/science.8009219
发表时间: 1994-06-24
期刊: SCIENCE
影响因子: 56.9
作者:
CLELAND, WW;KREEVOY, MM
通讯作者: KREEVOY, MM