$\require{mediawiki-texvc}$

연합인증

연합인증 가입 기관의 연구자들은 소속기관의 인증정보(ID와 암호)를 이용해 다른 대학, 연구기관, 서비스 공급자의 다양한 온라인 자원과 연구 데이터를 이용할 수 있습니다.

이는 여행자가 자국에서 발행 받은 여권으로 세계 각국을 자유롭게 여행할 수 있는 것과 같습니다.

연합인증으로 이용이 가능한 서비스는 NTIS, DataON, Edison, Kafe, Webinar 등이 있습니다.

한번의 인증절차만으로 연합인증 가입 서비스에 추가 로그인 없이 이용이 가능합니다.

다만, 연합인증을 위해서는 최초 1회만 인증 절차가 필요합니다. (회원이 아닐 경우 회원 가입이 필요합니다.)

연합인증 절차는 다음과 같습니다.

최초이용시에는
ScienceON에 로그인 → 연합인증 서비스 접속 → 로그인 (본인 확인 또는 회원가입) → 서비스 이용

그 이후에는
ScienceON 로그인 → 연합인증 서비스 접속 → 서비스 이용

연합인증을 활용하시면 KISTI가 제공하는 다양한 서비스를 편리하게 이용하실 수 있습니다.

Diastereoselective Synthesis of Unsaturated 1,4-Amino Alcohols as a Biologically Important Moiety 원문보기

Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea, v.28 no.4, 2005년, pp.382 - 390  

Jung Young Hoon (Organic & Medicinal Chemistry Laboratory, College of Pharmacy, Sungkyunkwan University) ,  Kim Ji Duck (Organic & Medicinal Chemistry Laboratory, College of Pharmacy, Sungkyunkwan University)

Abstract AI-Helper 아이콘AI-Helper

chial allylic ethers with a hydroxyl group attached to the $\pi-system$ and chlorosulfonyl isocyanate. The enantioselectivity of the CSI reaction with the chiral allylic and benzylic ethers was examined in various solvents and temperatures. Based on these results, it was proposed that the...

주제어

AI 본문요약
AI-Helper 아이콘 AI-Helper

* AI 자동 식별 결과로 적합하지 않은 문장이 있을 수 있으니, 이용에 유의하시기 바랍니다.

제안 방법

  • Next, this study tried to investigate the enantioselectivity in the reaction of the chiral allyl ethers with CSI (Scheme 4). First, an enantiomeric excess of the reaction of (S)-1- benzylcinnamyl methyl ether (7a) with CSI was observed at various solvents and temperatures.
  • , 1984; Yamamoto, 1992), it was found that the transition state in these mechanisms depends on the geometric configuration of the double bond. Therefore, the initial studies examined the reaction (2S, 5S)-c/s-allyl methyl ether 4a with CSI, in order to confirm the effect of the geometric configuration on the diastereoselectivity under the reaction condition. In contrast to previous results, this reaction gave a mixture of (1 S, 4S)너, 4-amino alcohol 5a as a m이or product and 1, 2-amino alcohol 6 (Kim et al.

이론/모형

  • For flash column chromatography, E, Merck Kieselgel 60 (230-400 mesh) was used. High-resolution mass spectra (니 RMS) were recorded on a JEOL, J MS-505 or JMS-600 spectrometer using the chemical ionization (Cl) method.
본문요약 정보가 도움이 되었나요?

참고문헌 (20)

  1. Cieplak, A. S., Stereochemistry of nucleophilic addition to cyclohexanone. The importance of two-electron stabilizing interactions. J. Am. Chem. Soc., 103, 4540-4552 (1981) 

  2. Dean, J. A. Lange's handbook of chemistry, 4th edition, McGraw- Hill Inc., pp. 5.91-5.125 (1972) 

  3. Fukuzawa, S-I., Takahashi, K., Kato, H., and Yamazaki, H., Asymmetric methoxyselenenylation of alkenes with chiral ferrocenylselenium reagents. J. Org. Chem., 62, 7711-7716 (1997) 

  4. Houk, K. N., Moses, S. R., Wu, Y. -D., Rondan, N. G., Jager, V., Schohe, R., and Fronczek, F. R., Stereoselective nitrile oxide cycloadditions to chiral allyl ethers and alcohols. The inside alkoxy effect. J. Am. Chem. Soc., 106, 3880-3882 (1984) 

  5. Johannsen, M. and Jorgensen, K. A., Allylic amination. Chem. Rev., 98, 1689-1708 (1998) 

  6. Jung, Y. H. and Kim, J. D., A novel synthetic method for $\alpha$ - amino acids from allyl ethers via N-allylcarbamates. Arch. Pharm. Res., 23, 574-578 (2000) 

  7. Jung, Y. H. and Kim, J. D., One-pot synthesis of cinnamylamines with various protecting groups from cinnamyl ethers. Arch. Pharm. Res., 24, 371-376 (2001) 

  8. Jung, Y. H. and Kim, J. D., Mechanism studies on the CSI reaction with allyl ethers by varying p-substituent. Arch. Pharm. Res., 26, 667-678 (2003) 

  9. Kim, J. D., Lee, M. H., Lee, M. J., and Jung, Y. H., Novel synthetic method for N-allylcarbamates from allyl ethers using chlorosulfonyl Isocyanate. Tetrahedron Lett., 41, 5073- 5076 (2000) 

  10. Kim, J. D., Lee, M. H., Han, G., Park, H., Zee, O. P., and Jung, Y. H., Synthesis of N-protected allylic amines from allyl ethers. Tetrahedron, 57, 8257-8266 (2001) 

  11. Kim, J. D., Han, G., Jeong, L. S., Park, H. -J., Zee, O. P., and Jung, Y. H., Study of the stability of carbocations by chlorosulfonyl isocyanate reaction with ethers. Tetrahedron, 58, 4395-4402 (2002) 

  12. Kim, J. D., Han, G., Zee, O. P., and Jung, Y. H., Deprotection of benzyl and p-methoxybenzyl ethers by chlorosulfonyl isocyanate-sodium hydroxide. Tetrahedron Lett., 44, 733-735 (2003) 

  13. Kim, J. D., Zee, O. P., and Jung, Y. H., Regioselective and diastereoselective allylic amination using chlorosulfonyl isocyanate. A novel asymmetric synthesis of unsaturated aromatic 1,2-amino alcohols. J. Org. Chem., 68, 3721-3724 (2003) 

  14. Kim, J. D., Kim, I. S., Jin, C. H., Zee, O. P., and Jung, Y. H., Diastereoselective synthesis of unsaturated 1,2-amino alcohols from $\alpha$ -hydroxy allyl ethers using chlorosulfonyl isocyanate. Tetrahedron Lett., in press (2005) 

  15. March, J., Advanced organic chemistry, 4th edition, John Wiley & Sons Inc., pp. 326-327 (1992) 

  16. Nicholas, G. M. and Molinski, T. F., Structures of cribochalines A and B, branched-chain methoxylaminoalkyl pyridines from the micronesian sponge, Cribochalina sp. Absolute configuration and enantiomeric purity of related O-methyl oximes. Tetrahedron, 56, 2921-2927 (2000) 

  17. Sykes, P., A guidebook to mechanism in organic chemistry, 6th edition, Longman Scientific & Technical, Singapore, pp. 90- 93 (1986) 

  18. Truong, M., Lecornue, F., and Fadel, A., First synthesis of (1S, 2S)- and (1R, 2R)-1-amino-2-isopropylcyclobutanecarboxylic acids by asymmetric Strecker reaction from 2-substituted cyclobutanones. Tetrahedron: Asymmetry, 14, 1063-1072 (2003) 

  19. Yamamoto, Y., Chounan, Y., Nishii, S., Ibuka, T., and Kitahara, H., Diastereoselectivity of the conjugate addition of organocopper reagents to $\gamma-alkoxy-\alpha,\beta-unsaturated$ carbonyl derivatives. Importance of the reagent type and the doublebond geometry. J. Am. Chem. Soc., 114, 7652-7660 (1992) 

  20. Wovkulich, P. M. and Uskokovic, M. R., Total synthesis of acosamine and daunosamine utilizing a diastereoselective intramolecular [3+2] cycloaddition. Tetrahedron, 41, 3455 (1985) 

관련 콘텐츠

오픈액세스(OA) 유형

FREE

Free Access. 출판사/학술단체 등이 허락한 무료 공개 사이트를 통해 자유로운 이용이 가능한 논문

섹션별 컨텐츠 바로가기

AI-Helper ※ AI-Helper는 오픈소스 모델을 사용합니다.

AI-Helper 아이콘
AI-Helper
안녕하세요, AI-Helper입니다. 좌측 "선택된 텍스트"에서 텍스트를 선택하여 요약, 번역, 용어설명을 실행하세요.
※ AI-Helper는 부적절한 답변을 할 수 있습니다.

선택된 텍스트

맨위로