Substituted 3-hydroxy-delta-lactones from epoxides

A method comprising the steps of:

• reacting an epoxide of formula:
• wherein:
• n is an integer between 0 and 3, inclusive;
• Ra, Rb, Rc, Rd and each R group are independently hydrogen;
• halogen;
• C1 to C20 alkyl;
• C2 to C20 alkenyl;
• C2 to C20 alkynyl;
• up to a C16 carbocycle;
• up to a C1-6 heterocycle;
• —C(R13)zH(3-z);
• or a polymer chain;
• or
• two or more of Ra, Rb, Rc, Rd, or R groups may be taken together with intervening atoms to form one or more optionally substituted rings optionally containing one or more heteroatoms, and any of Ra, Rb, Rc, Rd, and R may optionally be further substituted with one or more X groups;
• P′ is hydrogen or a hydroxyl protecting group;
• each occurrence of X is independently halogen;
• a phosphorus-containing moiety, —OR10;
• —OC(O)R13;
• —OC(O)OR13;
• —OC(O)NR11R12;
• —CN;
• —CNO;
• —C(O)R13;
• —C(O)OR13;
• —C(O)NR11R12;
• —C(R13)zH(3-z);
• —NR11C(O)R10;
• —NR11C(O)OR10;
• —NCO;
• —NR12SO2R13;
• —S(O)xR13;
• —S(O)2NR11R12;
• —NO2;
• —N3;
• —(CH2)kR14;
• —(CH2)k—Z—R14;
• and —(CH2)k—Z—(CH2)m—R14;
• R10 at each occurrence can be independently selected from the group consisting of:
• hydrogen;
• —C(R13)zH(3-z);
• C1 to C12 alkyl;
• C2 to C12 alkenyl;
• C2 to C12 alkynyl;
• up to a C12 carbocycle;
• up to a C12 heterocycle;
• —S(O)2R13;
• —Si(R15)3;
• and a hydroxyl protecting group;
• R11 and R12 at each occurrence can be independently selected from the group consisting of:
• hydrogen;
• C1 to C12 alkyl;
• C2 to C12 alkenyl;
• C2 to C12 alkynyl;
• and —C(R13)zH(3-z);
• R11 and R12;
• when both present, can optionally be taken together with the atom to which they are attached to form an optionally substituted 3- to 10-membered ring, optionally containing one or more additional heteroatoms;
• R13 at each occurrence can be independently selected from the group consisting of:
• hydrogen;
• halogen;
• C1 to C12 alkyl;
• C2 to C12 alkenyl;
• C2 to C12 alkynyl;
• up to a C12 carbocycle;
• or up to a C12 heterocycle;
• R14 at each occurrence can be independently selected from the group consisting of halogen;
• —OR10;
• —OC(O)R13;
• —OC(O)OR13;
• —OC(O)NR11R12;
• —CN;
• —CNO;
• —C(R13)zH(3-z);
• —C(O)R13;
• C(O)OR13;
• —C(O)NR11R12;
• —NR11C(O)R13;
• —NR11C(O)OR10;
• —NR11SO2R13;
• —NCO;
• —N3;
• —NO2;
• —S(O)xR13;
• —SO2NR11R12;
• up to a C12 heterocycle;
• and up to a C12 carbocycle;
• R15 at each occurrence can be independently selected from the group consisting of:
• C1 to C6 alkyl;
• C2 to C6 alkenyl;
• C2 to C6 alkynyl;
• and up to C12 substituted or unsubstituted carbocycle;
• Z is a divalent linker and can be selected from the group consisting of:
• —(CH═CH)a—;
• —(CH≡CH)a—;
• —C(O)—;
• —C(═NOR11)—;
• —C(═NNR11R12)—;
• —O—;
• —N(R11)—;
• —N(C(O)R13)—;
• —S(O)x—;
• a polyether;
• and a polyamine;
• a can be 1, 2, 3, or 4;
• k can be an integer from 1 to 8 inclusive;
• m can be an integer from 1 to 8 inclusive;
• x can be 0, 1, or 2;
• and
• z can be 1, 2, or 3;
• with carbon monoxide (CO) in the presence of a catalytically effective amount of a catalyst of the formula:
• [Lewis acid]u+{[QT(CO)v]s−}t II
• wherein:
• Q is any ligand or set of ligands and need not be present;
• T is a transition metal;
• s is an integer from 1 to 4 inclusive;
• t is a number such that t multiplied by s equals u;
• u is an integer from 1 to 6 inclusive;
• and
• v is an integer from 1 to 9 inclusive;
• to produce a compound of the formula: