Regioncontrolled formation of iodohy dnns and expoxides from Vic-diols
A novel method for the stereoselective preparation of iodohydrins and epoxides from stereogenic vicinal diols is described. This new high-yield methodology consists of the conversion of thionocarbonates such as 12 to the primary iodo derivative 14 with complete regiocontrol. Deprotection of the seco...
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| Published in: | Tetrahedron letters Vol. 36; no. 41; pp. 7367 - 7370 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
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Elsevier Ltd
09-10-1995
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| Abstract | A novel method for the stereoselective preparation of iodohydrins and epoxides from stereogenic vicinal diols is described. This new high-yield methodology consists of the conversion of thionocarbonates such as
12 to the primary iodo derivative
14 with complete regiocontrol. Deprotection of the secondary alcohol derivative in
14 gives the corresponding synthetically versatile iodohydrin
16, which is converted to epoxide
17. This methodology has been applied to complex tetraols
29 and
34. In the case of diols the transformation is conveniently carried out in high yield as a one-pot reaction.
A novel one-pot method for the stereoselective preparation of iodohydrins and epoxides from chiral vicinal diols is described. |
|---|---|
| AbstractList | A novel method for the stereoselective preparation of iodohydrins and epoxides from stereogenic vicinal diols is described. This new high-yield methodology consists of the conversion of thionocarbonates such as
12 to the primary iodo derivative
14 with complete regiocontrol. Deprotection of the secondary alcohol derivative in
14 gives the corresponding synthetically versatile iodohydrin
16, which is converted to epoxide
17. This methodology has been applied to complex tetraols
29 and
34. In the case of diols the transformation is conveniently carried out in high yield as a one-pot reaction.
A novel one-pot method for the stereoselective preparation of iodohydrins and epoxides from chiral vicinal diols is described. |
| Author | Khanapure, Subhash P. Hwang, Seong Woo Adiyaman, Mustafa Rokach, Joshua |
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| Cites_doi | 10.1016/S0040-4039(00)84764-4 10.1039/p19750001773 10.1021/jo00939a004 10.1021/ja00102a076 10.1021/cr00032a009 10.1021/jo00021a045 10.1016/S0040-4020(01)85362-X 10.1016/S0040-4039(00)87800-4 10.1016/S0040-4039(01)80807-8 10.1016/S0040-4039(01)90545-3 10.1139/v80-284 10.1021/jo00098a012 10.1016/S0040-4039(01)87038-6 10.1016/S0040-4020(01)88349-6 |
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| References | BIB9 Vedejs, Wu, Vedejs, Wu, Barton, Stick (BIB8) 1973; 39 Johnson, Sharpless, Jacobsen, Besse, Veschambree (BIB1) 1993; 50 Hwang, Adiyaman, Khanapure, Schio, Rokach (BIB7) 1994; 116 Kolb, Sharpless (BIB5) 1992; 48 Cimetiere, Jacob, Julia (BIB10) 1986; 27 Rokach, Zamboni, Lau, Guindon (BIB2) 1981; 22 Kolb, VanNieuwenhze, Sharpless (BIB3) 1994; 94 Just, Luthe (BIB4) 1980; 58 BIB13 BIB14 Le Merrer, Dureault, Gravier, Languin, Depezay (BIB12) 1985; 26 Masuda, Takase, Nishio, Hasegawa, Nishiyama, Ishii, Bonini, Righi, Sotgiu, Imamoto, Takeyama, Koto (BIB6) 1994; 59 BIB11 Cimetiere (10.1016/0040-4039(95)01658-9_BIB10) 1986; 27 Le Merrer (10.1016/0040-4039(95)01658-9_BIB12) 1985; 26 Kolb (10.1016/0040-4039(95)01658-9_BIB3) 1994; 94 Bonini (10.1016/0040-4039(95)01658-9_BIB6_2) 1991; 56 Hwang (10.1016/0040-4039(95)01658-9_BIB7) 1994; 116 Masuda (10.1016/0040-4039(95)01658-9_BIB6_1) 1994; 59 Vedejs (10.1016/0040-4039(95)01658-9_BIB8_1) 1973 Just (10.1016/0040-4039(95)01658-9_BIB4) 1980; 58 Johnson (10.1016/0040-4039(95)01658-9_BIB1_1) 1993 Rokach (10.1016/0040-4039(95)01658-9_BIB2) 1981; 22 Besse (10.1016/0040-4039(95)01658-9_BIB1_3) 1994; 50 Jacobsen (10.1016/0040-4039(95)01658-9_BIB1_2) 1993 Barton (10.1016/0040-4039(95)01658-9_BIB8_3) 1975 Imamoto (10.1016/0040-4039(95)01658-9_BIB6_3) 1986; 27 Kolb (10.1016/0040-4039(95)01658-9_BIB5) 1992; 48 Vedejs (10.1016/0040-4039(95)01658-9_BIB8_2) 1974; 39 |
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| Title | Regioncontrolled formation of iodohy dnns and expoxides from Vic-diols |
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