Asymmetric hetero diels-alder reaction of nitroso compounds utilizing tartaric acid ester as a chiral auxiliary

• Sakai Hiroki

• Ding Xia

• Yoshida Tetsusuke

• Fujinami Shuhei

• Ukaji Yutaka

• Inomata Katsuhiko

抄録

金沢大学金沢大学理工研究域物質化学系The regio- and enantioselective hetero Diels-Alder reaction of a nitroso compound with a cyclic dienol, cyclohexa-1,3-dienylmethanol, has been realized utilizing stoichiometric amount of tartaric acid ester as a chiral auxiliary to afford the corresponding dihydro-1,2-oxazine with complete regioselectivity and high enantioselectivity of up to 92% ee. A catalytic version of the asymmetric hetero Diels-Alder reaction of nitroso compounds with the dienol was also achieved to afford the corresponding optically active cycloadducts with up to 83% ee. The addition of MS 4A was crucial to realize reproducible high enantioselectivity. © 2008 The Japan Institute of Heterocyclic Chemistry All rights reserved.

収録刊行物

• Heterocycles

  Heterocycles 76 (2), 1285-1300, 2008-11-01

  日本複素環化学研究所 = The Japan Institute of Heterocyclic Chemistry

キーワード

• Cyclohexa-1,3-dienylmethanol
• Dihydro-1,2-oxazine
• Enantioselective
• Zinc Alkoxide

詳細情報

• CRID: 1574231877239413376
• NII論文ID: 120001170062
• NII書誌ID: AA00663739
• ISSN: 03855414
• Web Site: http://hdl.handle.net/2297/17050
• 本文言語コード: en
• データソース種別:
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