{"created":"2023-07-27T07:46:55.517481+00:00","id":21414,"links":{},"metadata":{"_buckets":{"deposit":"0b9c1fc3-90a3-4c50-ad9a-39a90a723412"},"_deposit":{"created_by":21,"id":"21414","owners":[21],"pid":{"revision_id":0,"type":"depid","value":"21414"},"status":"published"},"_oai":{"id":"oai:doshisha.repo.nii.ac.jp:00021414","sets":["4251:8393:8394:8395:8410","8:3372:3812:3827"]},"author_link":["15782","17752","17753","16542","17754","17755"],"item_1693811493084":{"attribute_name":"出版タイプ","attribute_value_mlt":[{"subitem_version_resource":"http://purl.org/coar/version/c_970fb48d4fbd8a85","subitem_version_type":"VoR"}]},"item_1694490770713":{"attribute_name":"権利者情報","attribute_value_mlt":[{"nameIdentifiers":[{"nameIdentifier":"DA03974933","nameIdentifierScheme":"AID"}],"rightHolderNames":[{"rightHolderLanguage":"ja","rightHolderName":"同志社大学理工学研究所"},{"rightHolderLanguage":"en","rightHolderName":"Science and Engineering Research Institute of Doshisha University"}]}]},"item_1_biblio_info_14":{"attribute_name":"書誌情報","attribute_value_mlt":[{"bibliographicIssueDates":{"bibliographicIssueDate":"2011-07-31","bibliographicIssueDateType":"Issued"},"bibliographicIssueNumber":"2","bibliographicPageEnd":"126","bibliographicPageStart":"113","bibliographicVolumeNumber":"52","bibliographic_titles":[{"bibliographic_title":"同志社大学理工学研究報告","bibliographic_titleLang":"ja"},{"bibliographic_title":"The Science and Engineering Review of Doshisha University","bibliographic_titleLang":"en"}]}]},"item_1_description_12":{"attribute_name":"抄録","attribute_value_mlt":[{"subitem_description":"キトサンはD-グルコサミンがβ-(1,4)結合した天然に大量に存在するバイオポリマーであるが、きわめて不溶なため化学的変換は困難である。一方、キトサンはキチンの脱アセチル化で選られ、酸性条件で可溶となる。これはまた、光学活性をもち、キラル源として利用することが期待される。キトサンのそのモノマーであるD-グルコサミンを有機溶媒に可溶化させるために変換して、アルデヒドへのジエチル亜鉛の不斉付加反応の配位子として用いることを検討した。まず、化学修飾キトサンを合成し、配位子としての利用を試みた。ベンズアルデヒドとジエチル亜鉛の反応でキチンやキトサンを用いるとラセミ体の1-フェニル-1-プロパノールを与えたが、N-フタロイル-6-O-トリチルキトサンを用いると反応は加速され、61%のエナンチオマー過剰率で(R)-1-フェニル-1-プロパノールが得られた。次に、D-(+)-グルコサミン誘導体を合成し、配位子として用いた。ベンジル-2-アセチルアミノ-4,6-O-アニシリデン-2-デオキシ-α-D-グルコピラノシドとチタン錯体が反応を加速し、各種アルデヒドとジエチル亜鉛の不斉付加反応において、高収率、94%に達するエナンチオ選択性で(R)-1-フェニル-1-プロパノールが得られ、最も効率のよい触媒であることが分かった。","subitem_description_language":"ja","subitem_description_type":"Abstract"},{"subitem_description":"Chitin is a naturally occurring biopolymer consisted of D-glucosamine with β-(1,4) bonds in large quantity but hardly used for chemical transformation because of its extremely low solubility. On the other hand, chitosan is easily obtained from chitin by deacetylation and soluble in acidic media. It is also optically active and expected to be used as a chiral source, if it is soluble in organic solvent. Chitosan and its monomer, D-(+)-glucosamine, were modified in order to become soluble in organic solvent and examined as a chiral ligand for asymmetric addition of diethylzinc to aldehydes. First, chemically modified chitosans were synthesized from chitosan, and tried to use as a ligand. Although the reaction of benzaldehyde with Et2Zn in the presence of chitin and chitosan gave the racemic 1-phenyl-1-propanol, N-phthaloyl-6-O-tritylchitosan as a ligand accelerated the reaction to produce (R)-1-phenyl-1-propanol with up to 61% ee. Next, D-(+)-glucosamine derivatives were synthesized and used as a ligand. Benzyl-2-acetylamino-4,6-O-anisylidene-2-deoxy-α-D-glucopyranoside and Ti complex accelerated the reaction and was found to be the most efficient catalyst for the asymmetric addition to the various aldehydes with diethylzinc, giving the (R)-1-phenyl-1-propanol in high yield and with high enantiomeric excess up to 94%.","subitem_description_language":"en","subitem_description_type":"Abstract"}]},"item_1_description_25":{"attribute_name":"フォーマット","attribute_value_mlt":[{"subitem_description":"application/pdf","subitem_description_type":"Other"}]},"item_1_identifier_registration":{"attribute_name":"ID登録","attribute_value_mlt":[{"subitem_identifier_reg_text":"10.14988/pa.2017.0000012467","subitem_identifier_reg_type":"JaLC"}]},"item_1_publisher_15":{"attribute_name":"出版者","attribute_value_mlt":[{"subitem_publisher":"同志社大学理工学研究所","subitem_publisher_language":"ja"}]},"item_1_publisher_16":{"attribute_name":"出版者（英）","attribute_value_mlt":[{"subitem_publisher":"Science and Engineering Research Institute of Doshisha University","subitem_publisher_language":"en"}]},"item_1_relation_24":{"attribute_name":"関連サイト","attribute_value_mlt":[{"subitem_relation_name":[{"subitem_relation_name_language":"ja","subitem_relation_name_text":"掲載刊行物所蔵情報へのリンク ／ Link to 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哲男 / 同志社大学生命医科学部医情報学科教授"},{"subitem_text_language":"ja","subitem_text_value":"前田, 憲輝 / Department of Molecular Science and Technology, Doshisha University"},{"subitem_text_language":"ja","subitem_text_value":"久次米, 亮 / Department of Molecular Science and Technology, Doshisha University"},{"subitem_text_language":"ja","subitem_text_value":"大江, 洋平 / 同志社大学生命医科学部医情報学科助教(有期)"},{"subitem_text_language":"ja","subitem_text_value":"山下, 隆之 / Department of Molecular Science and Technology, Doshisha University"},{"subitem_text_language":"ja","subitem_text_value":"古川, 功 / Department of Molecular Science and Technology, Doshisha University"}]},"item_1_text_9":{"attribute_name":"著者所属（英）","attribute_value_mlt":[{"subitem_text_language":"en","subitem_text_value":"Doshisha University"}]},"item_access_right":{"attribute_name":"アクセス権","attribute_value_mlt":[{"subitem_access_right":"open access","subitem_access_right_uri":"http://purl.org/coar/access_right/c_abf2"}]},"item_creator":{"attribute_name":"著者","attribute_type":"creator","attribute_value_mlt":[{"creatorNames":[{"creatorName":"太田, 哲男","creatorNameLang":"ja"},{"creatorName":"オオタ, テツオ","creatorNameLang":"ja-Kana"},{"creatorName":"Ohta, Tetsuo","creatorNameLang":"en"}],"nameIdentifiers":[{},{},{}]},{"creatorNames":[{"creatorName":"前田, 憲輝","creatorNameLang":"ja"},{"creatorName":"マエダ, ノリテル","creatorNameLang":"ja-Kana"},{"creatorName":"Maeda, Noriteru","creatorNameLang":"en"}],"nameIdentifiers":[{},{}]},{"creatorNames":[{"creatorName":"久次米, 亮","creatorNameLang":"ja"},{"creatorName":"クジメ, リョウ","creatorNameLang":"ja-Kana"},{"creatorName":"Kujime, Ryo","creatorNameLang":"en"}],"nameIdentifiers":[{},{}]},{"creatorNames":[{"creatorName":"Oe, Yohei","creatorNameLang":"en"},{"creatorName":"大江, 洋平","creatorNameLang":"ja"},{"creatorName":"オオエ, ヨウヘイ","creatorNameLang":"ja-Kana"}],"familyNames":[{},{},{}],"givenNames":[{},{},{}],"nameIdentifiers":[{},{},{}]},{"creatorNames":[{"creatorName":"山下, 隆之","creatorNameLang":"ja"},{"creatorName":"ヤマシタ, タカユキ","creatorNameLang":"ja-Kana"},{"creatorName":"Yamashita, Takayuki","creatorNameLang":"en"}],"nameIdentifiers":[{},{}]},{"creatorNames":[{"creatorName":"古川, 功","creatorNameLang":"ja"},{"creatorName":"フルカワ, イサオ","creatorNameLang":"ja-Kana"},{"creatorName":"Furukawa, Isao","creatorNameLang":"en"}],"nameIdentifiers":[{},{}]}]},"item_files":{"attribute_name":"ファイル情報","attribute_type":"file","attribute_value_mlt":[{"accessrole":"open_date","date":[{"dateType":"Available","dateValue":"2011-08-22"}],"displaytype":"detail","filename":"023052020004.pdf","filesize":[{"value":"340.2 kB"}],"format":"application/pdf","licensetype":"license_note","mimetype":"application/pdf","url":{"label":"023052020004.pdf","url":"https://doshisha.repo.nii.ac.jp/record/21414/files/023052020004.pdf"},"version_id":"8a7e28a3-e084-4997-b066-587f3ad3e67a"}]},"item_keyword":{"attribute_name":"キーワード","attribute_value_mlt":[{"subitem_subject":"キトサン","subitem_subject_language":"ja","subitem_subject_scheme":"Other"},{"subitem_subject":"グルコサミン","subitem_subject_language":"ja","subitem_subject_scheme":"Other"},{"subitem_subject":"不斉付加反応","subitem_subject_language":"ja","subitem_subject_scheme":"Other"},{"subitem_subject":"ジエチル亜鉛","subitem_subject_language":"ja","subitem_subject_scheme":"Other"},{"subitem_subject":"Chitosan","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"Glucosamine","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"Asymmetric Addition","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"Diethylzinc","subitem_subject_language":"en","subitem_subject_scheme":"Other"}]},"item_language":{"attribute_name":"言語","attribute_value_mlt":[{"subitem_language":"jpn"}]},"item_resource_type":{"attribute_name":"資源タイプ","attribute_value_mlt":[{"resourcetype":"departmental bulletin paper","resourceuri":"http://purl.org/coar/resource_type/c_6501"}]},"item_title":"キトサン,D-(+)-グルコサミン誘導体を配位子とする金属錯体存在下でのジエチル亜鉛の芳香族アルデヒド類への触媒的不斉付加反応","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"キトサン,D-(+)-グルコサミン誘導体を配位子とする金属錯体存在下でのジエチル亜鉛の芳香族アルデヒド類への触媒的不斉付加反応","subitem_title_language":"ja"},{"subitem_title":"キトサン D-(+)-グルコサミン ユウドウタイ オ ハイイシ トスル キンゾク サクタイ ソンザイカ デノ ジエチル アエン ノ ホウコウゾク アルデヒドルイ エノ ショクバイテキ フセイ フカ ハンノウ","subitem_title_language":"ja-Kana"},{"subitem_title":"Asymmetric addition of diethylzinc to aldehydes catalyzed by metal complexes with chitosan and D-(+)-Glucosamine derivatives as a ligand","subitem_title_language":"en"}]},"item_type_id":"1","owner":"21","path":["3827","8410"],"pubdate":{"attribute_name":"PubDate","attribute_value":"2011-08-22"},"publish_date":"2011-08-22","publish_status":"0","recid":"21414","relation_version_is_last":true,"title":["キトサン,D-(+)-グルコサミン誘導体を配位子とする金属錯体存在下でのジエチル亜鉛の芳香族アルデヒド類への触媒的不斉付加反応"],"weko_creator_id":"21","weko_shared_id":-1},"updated":"2024-03-01T01:37:30.532243+00:00"}